Quinoline derivatives microbicides containing these compounds, and their use for controlling bacteria and fungi

ABSTRACT

Quinoline derivatives of the formula    &lt;IMAGE&gt;  I  where R1, R2, R3 and R4 are hydrogen, methyl, halogen or nitro, R5 is a thiophene, pyrrole, oxazole, thiazole, imidazole, isoxazole, isothiazole, pyrazole, thiadiazole, oxadiazole or triazole radical which is substituted or unsubstituted, or is a substituted furan radical, and microbicidal agents containing these compounds.

The present invention relates to novel quinoline derivatives, processes for their preparation, microbicides which contain these compounds as active ingredients, and their use for controlling bacteria and fungi.

DE Nos. 3 225 169 and 2 005 959, GB No. 1 141 697 and EP-98 486 disclose that some 8-azolylcarbonyloxy-, 8-alphafuroyloxy- and 8-alpha-thenoyloxyquinoline derivatives can be used for controlling fungi, and some of them also for controlling bacteria. However, they do not always meet all the requirements, for example with regard to their microbicidal activity.

It is an object of the present invention to provide microbicidal compounds which are superior to the known ones in this respect.

We have found that this object is achieved, and that substituted quinoline derivatives of the formula ##STR2## where R¹ is hydrogen or methyl, R² is hydrogen or halogen, R³ is hydrogen, methyl, halogen or nitro, R⁴ is hydrogen, halogen or nitro and R⁵ is a thiophene, pyrrole, oxazole, thiazole, imidazole, isoxazole, isothiazole, pyrazole, 1,2,3-, 1,2,4-, 1,2,5- or 1,3,4-thiadiazole, 1,2,3-, 1,2,4-, 1,2,5- or 1,3,4-oxadiazole or 1,2,3- or 1,2,4-triazole radical which is unsubstituted or monosubstituted or disubstituted by C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, nitro or halogen, the substituents being independent of one another in the case of disubstitution, or is furan which is substituted by halogen or monosubstituted or disubstituted by methyl, and R³ and R⁴ are not simultaneously halogen, with the exception of 5-chloro-, 2-methyl- and 5-nitro-8-(1',2',3'-thiadiazole-4'-carbonyloxy)-quinoline, 5-chloro-8-(4'-methyl-1',2',3'-thiadiazole-5'-carbonyloxy)-quinoline, 5-methyl-, 5-methyl-7-nitro-, 5-methyl-7-halo- and 7-nitro-8-(alpha-thenoyloxy)-quinoline, 5-nitro- and 5-methyl-7-nitro-8-(2'-halofuroyl-5'-oxy)quinoline and 2-methyl-8-(isoxazole-5'-carbonyloxy)-quinoline, possess excellent microbicidal activity.

The heterocyclic structure R⁵ can be bonded to the remaining molecule at any possible position. R⁵ is a thien-2-yl, thien-3-yl, pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-oxadiazol-2-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-triazol-1-yl, 1,2,4-triazol-3-yl, 1,2,4-triazol-5-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,3-triazol-1-yl, 1,2,3-triazol-4-yl, 1,2,3-triazol-5-yl, 1,2,5-thiadiazol-3-yl or 1,2,5-oxadiazol-3-yl radical which is unsubstituted or monosubstituted or disubstituted by C₁ -C₄ -haloalkyl, nitro or halogen, the substituents being independent of one another in the case of disubstitution, or is a furan-2-yl or furan-3-yl radical which is substituted by halogen or monosubstituted or disubstituted by methyl. Halogen is preferably chlorine or bromine.

Preferred compounds of the formula I are those in which R¹ is hydrogen, R² is hydrogen or halogen, R³ is hydrogen, methyl, halogen or nitro, R⁴ is hydrogen, halogen or nitro and R⁵ is an unsubstituted or chloromethyl-substituted isoxazol-3-yl or isoxazol-5-yl radical, an unsubstituted or methyl-substituted oxazol-5-yl radical, an imidazol-1-yl radical or an unsubstituted or methyl-substituted 1,2,3-thiadiazol-4-yl or 1,2,3-thiadiazol-5-yl radical.

The compounds of the formula I are prepared, for example, by reacting a compound of the formula II ##STR3## where R¹, R², R³ and R⁴ have the stated meanings, or one of its alkali metal or alkaline earth metal salts with a carboxylic acid derivative of the formula III ##STR4## where R⁵ has the above meanings and A is a nucleophilically displaceable leaving group.

In the formula III, A is, for example, halogen, such as chlorine or bromine, alkoxycarbonyloxy, such as methoxycarbonyloxy or ethoxycarbonyloxy, benzyloxycarbonyloxy, azolyl, such as imidazolyl or triazolyl, or alkoxy, such as methoxy or ethoxy.

In a variant, the quinoline derivatives of the formula I, where R⁵ is azol-1-yl, can also be obtained by reacting a compound of the formula II, where R¹, R², R³ and R⁴ have the stated meanings, with a carbonylbisazole of the formula ##STR5## where B is one of the azol-1-yl radicals stated in claim 1 for R⁵.

Where carbonylbisimidazole and 8-hydroxyquinoline are used, the reaction can be represented by the following equation: ##STR6##

Although the reaction can also be carried out in the absence of solvents, it is advantageous to carry it out in an inert solvent or diluent. Examples of suitable solvents are:

halohydrocarbons, in particular chlorohydrocarbons, eg. tetrachloroethylene, 1,1,2,2- and 1,1,1,2-tetrachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, chloronaphthalene, dichloronaphthalene, carbon tetrachloride, 1,1,1- and 1,1,2-trichloroethane, trichloroethylene, pentachloroethane, o-, m- and p-difluorobenzene, 1,2-dichloroethane, 1,1-dichloroethane, 1,2-cis-dichloroethylene, chlorobenzene, fluorobenzene, bromobenzene, iodobenzene, o-, m- and p-dichlorobenzene, o-, p- and m-dibromobenzene, o-, m- and p-chlorotoluene or 1,2,4-trichlorobenzene; ethers, eg. ethyl propyl ether, methyl tert-butyl ether, n-butyl ether ether, di-n-butyl ether, diisobutyl ether, diisoamyl ether, diisopropyl ether, anisole, phenetole, cyclohexyl methyl ether, diethyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, dioxane, thioanisole or β,β'-dichlorodiethyl ether; nitrohydrocarbons, such as nitromethane, nitroethane, nitrobenzene, o-, m- and p-chloronitrobenzene or o-nitrotoluene; nitriles, such as acetonitrile, butyro- nitrile, isobutyronitrile, benzonitrile or m-chlorobenzonitrile; aliphatic and cycloaliphatic hydrocarbons, eg. heptane, pinane, nonane, o-, m- and p-cymene, gasoline fractions boiling within a range from 70° to 190° C., cyclohexane, methylcyclohexane, decalin, petroleum ether, hexane, naphtha, 2,2,4-trimethylpentane, 2,2,3-trimethylpentane, 2,3,3-trimethylpentane or octane; esters, eg. ethyl acetate, ethyl acetoacetate or isobutyl acetate; amides, eg. formamide, methyl formamide or dimethyl formamide; ketones, eg. acetone or methyl ethyl ketone, and, if appropriate, also water and mixtures of these. Advantageously, the solvent is used in an amount of from 100 to 2000, preferably from 200 to 900, % by weight, based on starting material II.

Where A is halogen, it is advisable, although not essential, to carry out the reaction in the presence of an acid acceptor. Suitable acid acceptors are all conventional ones. These preferably include tertiary amines, alkaline earth metal compounds, ammonium compounds and alkali metal compounds, as well as mixtures of these. However, zinc compounds can also be used. Examples of suitable basic compounds are potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate, lithium hydroxide, lithium carbonate, sodium bicarbonate, potassium bicarbonate, calcium hydroxide, barium oxide, magnesium hydroxide, magnesium oxide, barium hydroxide, calcium carbonate, magnesium carbonate, magnesium acetate, zinc hydroxide, zinc oxide, zinc carbonate, zinc acetate, sodium formate, sodium acetate, trimethylamine, triethylamine, tripropylamine, triisopropylamine, tributylamine, triisobutylamine, tri-sec-butylamine, tri-tert-butylamine, tribenzylamine, tricyclohexylamine, triamylamine, trihexylamine, N,N-dimethylaniline, N,N-diethylaniline, N,N-dipropylaniline, N,N-dimethyltoluidine, N,N-diethyltoluidine, N,N-dipropyltoluidine, N,N-dimethyl-p-aminopyridine, N,N-diethyl-p-aminopyridine, N,N-dipropyl-p-aminopyridine, N-methylpyrrolidone, N-ethylpyrrolidone, N-metylpiperidine, N-ethylpiperidine, N-methylpyrrolidine, N-ethylpyrrolidine, N-methylimidazole, N-ethylimidazole, N-methylpyrrole, N-ethylpyrrole, N-methylmorpholine, N-ethylmorpholine, N-methylhexamethyleneimine, N-ethylhexamethyleneimine, pyridine, quinoline, alpha-picoline, gamma-picoline, isoquinoline, pyrimidine, acridine, N,N,N'N'-tetramethylethylenediamine, N,N,N'N'-tetraethylethylenediamine, quinoxaline, quinazoline, N-propyldiisopropylamine, N,N-dimethylcyclohexylamine, 2,6-lutidine, 2,4-lutidine, trifurfurylamine and triethylenediamine.

The hydrogen halide, for example, formed during the reaction can, however, also be removed by passing in an inert gas, eg. nitrogen.

The process for the preparation of the novel compounds is advantageously carried out as follows: the starting material II, if necessary in one of the above-mentioned diluents, is initially taken, and the starting material III or IV and, if required, an acid acceptor are then added simultaneously or in succession. However, it is also possible for the starting material III or IV in one of the abovementioned diluents to be initially taken and then the starting material II and, if required, an acid acceptor to be added, simultaneously or in any order, via two separate feeds.

In many cases, the reaction is complete as soon as the components have been added; in other cases, the reaction is completed by stirring for a further 10 minutes to 14 hours at from -10° to 120° C., preferably from 0° to 100° C., in particular from 20° to 80° C.

The compound I is isolated from the reaction mixture in a conventional manner, for example by distilling off the solvent or excess starting material III, or directly by filtration under suction. In this case, the remaining residue is washed with water or dilute alkali or acid in order to remove acidic or basic impurities, and is dried. In the case of water-immiscible diluents, the reaction mixture can also be extracted directly with water or with dilute alkali or acid and then dried and evaporated down. However, it is also possible to dissolve the residue in a water-immiscible solvent and to wash the solution as described above. The desired end products are obtained in pure form; if necessary, they can be further purified by recrystallization, chromatography or distillation.

In the Preparation Examples and Examples of use, parts and percentages are by weight.

Preparation Examples

EXAMPLE 1

5.1 parts of triethylamine were added to a stirred mixture of 13.5 parts of 7-bromo-5-nitro-8-hydroxyquinoline in 135 parts of ethyl acetate at from 15° to 25° C. in the course of 5 minutes, and the mixture was stirred for 5 minutes. 7.4 parts of 1,2,3-thiadiazole-4-carbonyl chloride were then added at from 20° to 25° C. in the course of 10 minutes, while stirring, and stirring was continued for 2 hours at 50° C. The reaction mixture was evaporated to dryness under reduced pressure, and the residue was dispersed in 400 parts of 0.5N hydrochloric acid in the course of 5 minutes. The undissolved material was filtered off under suction, and the filtrate was washed with water and stirred in 200 parts of 1N sodium hydroxide solution for 10 minutes. Filtration under suction, washing with water and drying gave 13 parts of 7-bromo- 5-nitro-8-(1',2',3'-thiadiazole-4'-carbonyl)-oxyquinoline of melting point 192°-194° C.

EXAMPLE 2

6.52 parts of 2-methylpyridine were added to a stirred mixture of 15.7 parts of 7-chloro-5-nitro-8-hydroxyquinoline in 190 parts of 1,2-dichloroethane at 25° C. in the course of 5 minutes, and the mixture was stirred for 5 minutes. 9.2 parts of isoxazole-5-carbonyl chloride were then added at from 20° to 25° C. in the course of 10 minutes, while stirring, and stirring was continued for 3 hours at 55° C. The reaction mixture was evaporated to dryness under reduced pressure, and the residue was stirred in 200 parts of 0.5N hydrochloric acid for 5 minutes. The precipitate was filtered off under suction, washed with water and stirred for 10 minutes in 200 parts of dilute sodium carbonate solution. Filtration under suction, washing with water at 60° C. and drying gave 17.5 parts of 7-chloro-5-nitro-8-(isoxazole-5'-carbonyl)-oxyquinoline of melting point 132°-134° C.

EXAMPLE 3

29 parts of 8-hydroxyquinoline in 65 parts of tetrahydrofuran were added to a stirred solution of 32.4 parts of 1,1-carbonylbisimidazole in 120 parts of tetrahydrofuran at from 20° to 25° C. in the course of 3 minutes, and the mixture was stirred for 12 hours at room temperature. The precipitate which separated out was filtered off under suction, washed with diethyl ether and water in succession and dried. 21 parts of 8-(imidazole-1'-carbonyl)-oxyquinoline of melting point 137°-141° C. were obtained.

The following Examples can be prepared in a similar manner:

    __________________________________________________________________________     No.  R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                           R.sup.4                                                                           R.sup.5        m.p. [°C.]                              __________________________________________________________________________     4    H  H  H  Cl thenyl-2                                                      5    H  H  H  Cl thenyl-3                                                      6    H  H  H  Cl 2-chlorothenyl-3                                              7    H  H  H  Cl 5-chlorothenyl-2                                              8    H  H  H  Cl 5-nitrothenyl-2                                               9    H  H  H  Cl 4-methylthenyl-2                                              10   H  H  H  Cl 3-methylthenyl-2                                              11   H  H  H  Cl 2-methylthenyl-3                                              12   H  H  H  Cl 3-methylthenyl-4                                              13   H  H  H  Cl 2,5-dimethylthenyl-4                                          14   H  H  H  Cl 2,3-dichlorothenyl-4                                          15   H  H  H  Cl 5-methylthenyl-2                                              16   H  H  H  Cl pyrryl-2                                                      17   H  H  H  Cl pyrryl-3                                                      18   H  H  H  Cl 3-methylpyrryl-2                                              19   H  H  H  Cl 2-methylpyrryl-3                                              20   H  H  H  Cl 5-chloropyrryl-2                                              21   H  H  H  Cl oxazolyl-2                                                    22   H  H  H  Cl oxazolyl-4                                                    23   H  H  H  Cl oxazolyl-5                                                    24   H  H  H  Cl 1,2,3-thiadiazolyl-4                                                                          121-123                                        25   H  H  H  Cl 4-methyloxazolyl-5                                            26   H  H  H  Cl 2-methyloxazolyl-5                                            27   H  H  H  Cl thiazolyl-2                                                   28   H  H  H  Cl thiazolyl-4                                                   29   H  H  H  Cl thiazolyl-5                                                   30   H  H  H  Cl 4-methylthiazolyl-5                                           31   H  H  H  Cl 2-methylthiazolyl-5                                           32   H  H  H  Cl imidazolyl-4                                                  33   H  H  H  Cl imidazolyl-5                                                  34   H  H  H  Cl 4-methylimidazolyl-5                                          35   H  H  H  Cl 1-methylimidazolyl-5                                          36   H  H  H  Cl 4-nitroimidazolyl-1                                           37   H  H  H  Cl 2-methyl-4-nitroimidazolyl-1                                  38   H  H  H  Cl 4,5-dichloroimidazolyl-1                                      39   H  H  H  Cl 1-methylpyrryl-2                                              40   H  H  H  Cl isoxazolyl-3   93-96                                          41   H  H  H  Cl isoxazolyl-4                                                  42   H  H  H  Cl isoxazolyl-5   101-104                                        43   H  H  H  Cl 5-chloromethylisoxazolyl-3                                                                    151-152                                        44   H  H  H  Cl isothiazolyl-3                                                45   H  H  H  Cl isothiazolyl-4                                                46   H  H  H  Cl isothiazolyl-5                                                47   H  H  H  Cl 4-methylisothiazolyl-5                                        48   H  H  H  Cl pyrazolyl-4                                                   49   H  H  H  Cl pyrazolyl-5                                                   50   H  H  H  Cl 4-chloropyrazolyl-5                                           51   H  H  H  Cl 1-methylpyrazolyl-5                                           52   H  H  H  Cl 1,2,3-thiadiazolyl-5                                          53   H  H  H  Cl 1,2,3-oxadiazolyl-5                                           54   H  H  H  Cl 1,2,3-oxadiazolyl-4                                           55   H  H  H  Cl 5-methyl-1,2,3-oxadiazolyl-4                                  56   H  H  H  Cl 4-methyl-1,2,3-oxadiazolyl-5                                  57   H  H  H  Cl 1,3,4-thiadiazolyl-2                                          58   H  H  H  Cl 2-methyl-1,3,4-thiadiazolyl-5                                 59   H  H  H  Cl 1,2,4-thiadiazolyl-3                                          60   H  H  H  Cl 1,2,4-thiadiazolyl-5                                          61   H  H  H  Cl 3-methyl-1,2,4-thiadiazolyl-5                                 62   H  H  H  Cl 1,2,4-oxadiazolyl-3                                           63   H  H  H  Cl 1,2,4-oxadiazolyl-5                                           64   H  H  H  Cl 1,2,4-triazolyl-5                                             65   H  H  H  Cl 1,2,4-triazolyl-3                                             66   H  H  H  Cl 1,3,4-oxadiazolyl-5                                           67   H  H  H  Cl 2-methyl-1,3,4-oxadiazolyl-5                                  68   H  H  H  Cl 2-chloro-1,3,4-oxadiazolyl-5                                  69   H  H  H  Cl 1,2,5-oxadiazolyl-3                                           70   H  H  H  Cl 3-methyl-1,2,5-oxadiazolyl-4                                  71   H  H  H  Cl 1,2,5-thiadiazolyl-3                                          72   H  H  H  Cl 3-methyl-1,2,5-thiadiazolyl-4                                 73   H  H  H  Cl 2-methylfuryl-5                                               74   H  H  H  Cl 2,5-dimethylfuryl-4                                                                           111-114                                        75   H  H  H  Cl 2-chlorofuryl-5                                               76   H  H  H  Cl 5-methyloxazolyl-4                                            77   H  H  H  Cl 4-methyloxazolyl-2                                            78   H  H  H  Cl 2-bromofuryl-5                                                79   H  H  H  Cl 2-methylfuryl-4                                               80   H  H  H  Cl 5-methylisoxazolyl-3                                          81   H  H  H  Cl 4-methylisoxazolyl-3                                          82   H  H  H  Cl 5-methylisothiazolyl-3                                        83   H  H  H  Cl 4-methylisothiazolyl-3                                        84   H  H  H  Cl 5-methyl-1,2,3-thiadiazolyl-4                                 85   H  H  H  Cl 4-methyl-1,2,3-thiadiazolyl-5                                                                 162-164                                        86   H  H  H  Cl pyrryl-1                                                      87   H  H  H  Cl imidazolyl-1                                                  88   H  H  H  Cl pyrazolyl-1                                                   89   H  H  H  Cl 1,3,4-triazolyl-1                                             90   H  H  H  Cl 1,2,4-triazolyl-1                                             91   H  H  H  Br thenyl-2                                                      92   H  H  H  Br thenyl-3                                                      93   H  H  H  Br 2-chlorothenyl-3                                              94   H  H  H  Br 5-chlorothenyl-2                                              95   H  H  H  Br 5-nitrothenyl-2                                               96   H  H  H  Br 4-methylthenyl-2                                              97   H  H  H  Br 3-methylthenyl-2                                              98   H  H  H  Br 2-methylthenyl-3                                              99   H  H  H  Br 3-methylthenyl-4                                              100  H  H  H  Br 2,5-dimethylthenyl-4                                          101  H  H  H  Br 2,3-dichlorothenyl-4                                          102  H  H  H  Br 5-methylthenyl-2                                              103  H  H  H  Br pyrryl-2                                                      104  H  H  H  Br pyrryl-3                                                      105  H  H  H  Br 3-methylpyrryl-2                                              106  H  H  H  Br 2-methylpyrryl-3                                              107  H  H  H  Br 5-chloropyrryl-2                                              108  H  H  H  Br oxazolyl-2                                                    109  H  H  H  Br oxazolyl-4                                                    110  H  H  H  Br oxazolyl-5                                                    111  H  H  H  Br 1,2,3-thiadiazolyl-4                                                                          127-130                                        112  H  H  H  Br 4-methyloxazolyl-5                                            113  H  H  H  Br 2-methyloxazolyl-5                                            114  H  H  H  Br thiazolyl-2                                                   115  H  H  H  Br thiazolyl-4                                                   116  H  H  H  Br thiazolyl-5                                                   117  H  H  H  Br 4-methylthiazolyl-5                                           118  H  H  H  Br 2-methylthiazolyl-5                                           119  H  H  H  Br imidazolyl-4                                                  120  H  H  H  Br imidazolyl-5                                                  121  H  H  H  Br 4-methylimidazolyl-5                                          122  H  H  H  Br 1-methylimidazolyl-5                                          123  H  H  H  Br 4-nitroimidazolyl-1                                           124  H  H  H  Br 2-methyl-4-nitroimidazolyl-1                                  125  H  H  H  Br 4,5-dichloroimidazolyl-1                                      126  H  H  H  Br 1-methylpyrryl-2                                              127  H  H  H  Br isoxazolyl-3   126-128                                        128  H  H  H  Br isoxazolyl-4                                                  129  H  H  H  Br isoxazolyl-5                                                  130  H  H  H  Br 5-chloromethylisoxazolyl-3                                                                    148-151                                        131  H  H  H  Br isothiazolyl-3                                                132  H  H  H  Br isothiazolyl-4                                                133  H  H  H  Br isothiazolyl-5                                                134  H  H  H  Br 4-methylisothiazolyl-5                                        135  H  H  H  Br pyrazolyl-4                                                   136  H  H  H  Br pyrazolyl-5                                                   137  H  H  H  Br 4-chloropyrazolyl-5                                           138  H  H  H  Br 1-methylpyrazolyl-5                                           139  H  H  H  Br 1,2,3-thiadiazolyl-5                                          140  H  H  H  Br 1,2,3-oxadiazolyl-5                                           141  H  H  H  Br 1,2,3-oxadiazolyl-4                                           142  H  H  H  Br 5-methyl-1,2,3-oxadiazolyl-4                                  143  H  H  H  Br 4-methyl-1,2,3-oxadiazolyl-5                                  144  H  H  H  Br 1,3,4-thiadiazolyl-2                                          145  H  H  H  Br 2-methyl-1,3,4-thiadiazolyl-5                                 146  H  H  H  Br 1,2,4-thiadiazolyl-3                                          147  H  H  H  Br 1,2,4-thiadiazolyl-5                                          148  H  H  H  Br 3-methyl-1,2,4-thiadiazolyl-5                                 149  H  H  H  Br 1,2,4-oxadiazolyl-3                                           150  H  H  H  Br 1,2,4-oxadiazolyl-5                                           151  H  H  H  Br 1,2,4-triazolyl-5                                             152  H  H  H  Br 1,2,4-triazolyl-3                                             153  H  H  H  Br 1,3,4-oxadiazolyl-5                                           154  H  H  H  Br 2-methyl-1,3,4-oxadiazolyl-5                                  155  H  H  H  Br 2-chloro-1,3,4-oxadiazolyl-5                                  156  H  H  H  Br 1,2,5-oxadiazolyl-3                                           157  H  H  H  Br 3-methyl-1,2,5-oxadiazolyl-4                                  158  H  H  H  Br 1,2,5-thiadiazolyl-3                                          159  H  H  H  Br 3-methyl-1,2,5-thiadiazolyl-4                                 160  H  H  H  Br 2-methyl-furyl-5                                              161  H  H  H  Br 2,5-dimethylfuryl-4                                                                           159- 161                                       162  H  H  H  Br 2-chlorofuryl-5                                               163  H  H  H  Br 5-methyl-oxazolyl-4                                           164  H  H  H  Br 4-methyl-oxazolyl-2                                           165  H  H  H  Br 2-bromofuryl-5                                                166  H  H  H  Br 2-methylfuryl-4                                               167  H  H  H  Br 5-methylisoxazolyl-3                                          168  H  H  H  Br 4-methylisoxazolyl-3                                          169  H  H  H  Br 5-methylisothiazolyl-3                                        170  H  H  H  Br 4-methylisothiazolyl-3                                        171  H  H  H  Br 5-methyl-1,2,3-thiadiazolyl-4                                 172  H  H  H  Br 4-methyl-1,2,3-thiadiazolyl-5                                                                 184-185                                        173  H  H  H  Br pyrryl-1                                                      174  H  H  H  Br imidazolyl-1                                                  175  H  H  H  Br pyrazolyl-1                                                   176  H  H  H  Br 1,3,4-triazolyl-1                                             177  H  H  H  Br 1,2,4-triazolyl-1                                             178  H  H  H  NO.sub.2                                                                          2-chlorothenyl-3                                              179  H  H  H  NO.sub.2                                                                          5-chlorothenyl-2                                              180  H  H  H  NO.sub.2                                                                          5-nitrothenyl-2                                               181  H  H  H  NO.sub.2                                                                          4-methylthenyl-2                                              182  H  H  H  NO.sub.2                                                                          3-methylthenyl-2                                              183  H  H  H  NO.sub.2                                                                          2-methylthenyl-3                                              184  H  H  H  NO.sub.2                                                                          3-methylthenyl-4                                              185  H  H  H  NO.sub.2                                                                          2,5-dimethylthenyl-4                                          186  H  H  H  NO.sub.2                                                                          2,3-dichlorothenyl-4                                          187  H  H  H  NO.sub.2                                                                          5-methylthenyl-2                                              188  H  H  H  NO.sub.2                                                                          pyrryl-2                                                      189  H  H  H  NO.sub.2                                                                          pyrryl-3                                                      190  H  H  H  NO.sub.2                                                                          3-methylpyrryl-2                                              191  H  H  H  NO.sub.2                                                                          2-methylpyrryl-3                                              192  H  H  H  NO.sub.2                                                                          5-chloropyrryl-2                                              193  H  H  H  NO.sub.2                                                                          oxazolyl-2                                                    194  H  H  H  NO.sub.2                                                                          oxazolyl-4                                                    195  H  H  H  NO.sub.2                                                                          oxazolyl-5                                                    196  H  H  H  NO.sub.2                                                                          1,2,3-thiadiazolyl-4                                                                          198 Decomp.                                    197  H  H  H  NO.sub.2                                                                          4-methyloxazolyl-5                                            198  H  H  H  NO.sub.2                                                                          2-methyloxazolyl-5                                            199  H  H  H  NO.sub.2                                                                          thiazolyl-2                                                   200  H  H  H  NO.sub.2                                                                          thiazolyl-4                                                   201  H  H  H  NO.sub.2                                                                          thiazolyl-5                                                   202  H  H  H  NO.sub.2                                                                          4-methylthiazolyl-5                                           203  H  H  H  NO.sub.2                                                                          2-methylthiazolyl-5                                           204  H  H  H  NO.sub.2                                                                          imidazolyl-4                                                  205  H  H  H  NO.sub.2                                                                          imidazolyl-5                                                  206  H  H  H  NO.sub.2                                                                          4-methylimidazolyl-5                                          207  H  H  H  NO.sub.2                                                                          1-methylimidazolyl-5                                          208  H  H  H  NO.sub.2                                                                          4-nitroimidazolyl-1                                           209  H  H  H  NO.sub.2                                                                          2-methyl-4-nitroimidazolyl-1                                  210  H  H  H  NO.sub.2                                                                          4,5-dichloroimidazolyl-1                                      211  H  H  H  NO.sub.2                                                                          1-methylpyrryl-2                                              212  H  H  H  NO.sub.2                                                                          isoxazolyl-5   153-154                                        213  H  H  H  NO.sub.2                                                                          isoxazolyl-4                                                  214  H  H  H  NO.sub.2                                                                          isoxazolyl-5   168-170                                        215  H  H  H  NO.sub.2                                                                          5-chloromethylisoxazolyl-3                                                                    129-131                                        216  H  H  H  NO.sub.2                                                                          isothiazolyl-3                                                217  H  H  H  NO.sub.2                                                                          isothiazolyl-4                                                218  H  H  H  NO.sub.2                                                                          isothiazolyl-5                                                219  H  H  H  NO.sub.2                                                                          4-methylisothiazolyl-5                                        220  H  H  H  NO.sub.2                                                                          pyrazolyl-4                                                   221  H  H  H  NO.sub.2                                                                          pyrazolyl-5                                                   222  H  H  H  NO.sub.2                                                                          4-chloropyrazolyl-5                                           223  H  H  H  NO.sub.2                                                                          1-methylpyrazolyl-5                                           224  H  H  H  NO.sub.2                                                                          1,2,3-thiadiazolyl-5                                          225  H  H  H  NO.sub.2                                                                          1,2,3-oxadiazolyl-5                                           226  H  H  H  NO.sub.2                                                                          1,2,3-oxadiazolyl-4                                           227  H  H  H  NO.sub.2                                                                          5-methyl-1,2,3-oxadiazolyl-4                                  228  H  H  H  NO.sub.2                                                                          4-methyl-1,2,3-oxadiazolyl-5                                  229  H  H  H  NO.sub.2                                                                          1,3,4-thiadiazolyl-2                                          230  H  H  H  NO.sub.2                                                                          2-methyl-1,3,4-thiadiazolyl-5                                 231  H  H  H  NO.sub.2                                                                          1,2,4-thiadiazolyl-3                                          232  H  H  H  NO.sub.2                                                                          1,2,4-thiadiazolyl-5                                          233  H  H  H  NO.sub.2                                                                          3-methyl-1,2,4-thiadiazolyl-5                                 234  H  H  H  NO.sub.2                                                                          1,2,4-oxadiazolyl-3                                           235  H  H  H  NO.sub.2                                                                          1,2,4-oxadiazolyl-5                                           236  H  H  H  NO.sub.2                                                                          1,2,4-triazolyl-5                                             237  H  H  H  NO.sub.2                                                                          1,2,4-triazolyl-3                                             238  H  H  H  NO.sub.2                                                                          1,3,4-oxadiazolyl-5                                           239  H  H  H  NO.sub.2                                                                          2-methyl-1,3,4-oxadiazolyl-5                                  240  H  H  H  NO.sub.2                                                                          2-chloro-1,3,4-oxadiazolyl-5                                  241  H  H  H  NO.sub.2                                                                          1,2,5-oxadiazolyl-3                                           242  H  H  H  NO.sub.2                                                                          3-methyl-1,2,5-oxadiazolyl-4                                  243  H  H  H  NO.sub.2                                                                          1,2,5-thiadiazolyl-3                                          244  H  H  H  NO.sub.2                                                                          3-methyl-1,2,5-thiadiazolyl-4                                 245  H  H  H  NO.sub.2                                                                          2-methylfuryl-5                                               246  H  H  H  NO.sub.2                                                                          2,5-dimethylfuryl-4                                                                           156-157                                        247  H  H  H  NO.sub.2                                                                          2-chlorofuryl-5                                               248  H  H  H  NO.sub.2                                                                          5-methyloxazolyl-4                                            249  H  H  H  NO.sub.2                                                                          4-methyloxazolyl-2                                            250  H  H  H  NO.sub.2                                                                          2-bromofuryl-5                                                251  H  H  H  NO.sub.2                                                                          2-methylfuryl-4                                               252  H  H  H  NO.sub.2                                                                          5-methylisoxazolyl-3                                          253  H  H  H  NO.sub.2                                                                          4-methylisoxazolyl-3                                          254  H  H  H  NO.sub.2                                                                          5-methylisothiazolyl-3                                        255  H  H  H  NO.sub.2                                                                          4-methylisothiazolyl-3                                        256  H  H  H  NO.sub.2                                                                          4-methyl-1,2,3-thiadiazolyl-5                                                                 154-155                                        257  H  H  H  NO.sub.2                                                                          5-methyl-1,2,3-thiadiazolyl-4                                 258  H  H  H  NO.sub.2                                                                          pyrryl-1                                                      259  H  H  H  NO.sub.2                                                                          imidazolyl-1                                                  260  H  H  H  NO.sub.2                                                                          pyrazolyl-1                                                   261  H  H  H  NO.sub.2                                                                          1,3,4-triazolyl-1                                             262  H  H  H  NO.sub.2                                                                          1,2,4-triazolyl-1                                             263  H  H  NO.sub.2                                                                          H  thenyl-2                                                      264  H  H  NO.sub.2                                                                          H  thenyl-3                                                      265  H  H  NO.sub.2                                                                          H  2-chlorothenyl-3                                              266  H  H  NO.sub.2                                                                          H  5-chlorothenyl-2                                              267  H  H  NO.sub.2                                                                          H  5-nitrothenyl-2                                               268  H  H  NO.sub.2                                                                          H  4-methylthenyl-2                                              269  H  H  NO.sub.2                                                                          H  3-methylthenyl-2                                              270  H  H  NO.sub.2                                                                          H  2-methylthenyl-3                                              271  H  H  NO.sub.2                                                                          H  3-methylthenyl-4                                              272  H  H  NO.sub.2                                                                          H  2,5-dimethylthenyl-4                                          273  H  H  NO.sub.2                                                                          H  2,3-dichlorothenyl-4                                          274  H  H  NO.sub.2                                                                          H  5-methylthenyl-2                                              275  H  H  NO.sub.2                                                                          H  pyrryl-2                                                      276  H  H  NO.sub.2                                                                          H  pyrryl-3                                                      277  H  H  NO.sub.2                                                                          H  3-methylpyrryl-2                                              278  H  H  NO.sub.2                                                                          H  2-methylpyrryl-3                                              279  H  H  NO.sub.2                                                                          H  5-chloropyrryl-2                                              280  H  H  NO.sub.2                                                                          H  oxazolyl-2                                                    281  H  H  NO.sub.2                                                                          H  oxazolyl-4                                                    282  H  H  NO.sub.2                                                                          H  oxazolyl-5                                                    283  H  H  NO.sub.2                                                                          H  4-methyloxazolyl-5                                            284  H  H  NO.sub.2                                                                          H  2-methyloxazolyl-5                                            285  H  H  NO.sub.2                                                                          H  thiazolyl-2                                                   286  H  H  NO.sub.2                                                                          H  thiazolyl-4                                                   287  H  H  NO.sub.2                                                                          H  thiazolyl-5                                                   288  H  H  NO.sub.2                                                                          H  4-methylthiazolyl-5                                           289  H  H  NO.sub.2                                                                          H  2-methylthiazolyl-5                                           290  H  H  NO.sub.2                                                                          H  imidazolyl-4                                                  291  H  H  NO.sub.2                                                                          H  imidazolyl-5                                                  292  H  H  NO.sub.2                                                                          H  4-methylimidazolyl-5                                          293  H  H  NO.sub.2                                                                          H  1-methylimidazolyl-5                                          294  H  H  NO.sub.2                                                                          H  4-nitroimidazolyl-1                                           295  H  H  NO.sub.2                                                                          H  2-methyl-4-nitroimidazolyl-1                                  296  H  H  NO.sub.2                                                                          H  4,5-dichloroimidazolyl-1                                      297  H  H  NO.sub.2                                                                          H  1-methylpyrryl-2                                              298  H  H  NO.sub.2                                                                          H  isoxazolyl-3   150-152                                        299  H  H  NO.sub.2                                                                          H  isoxazolyl-4                                                  300  H  H  NO.sub.2                                                                          H  isoxazolyl-5   167-169                                        301  H  H  NO.sub.2                                                                          H  5-chloromethylisoxazolyl-3                                                                    129-131                                        302  H  H  NO.sub.2                                                                          H  isothiazolyl-3                                                303  H  H  NO.sub.2                                                                          H  isothiazolyl-4                                                304  H  H  NO.sub.2                                                                          H  isothiazolyl-5                                                305  H  H  NO.sub.2                                                                          H  4-methylisothiazolyl-5                                        306  H  H  NO.sub.2                                                                          H  pyrazolyl-4                                                   307  H  H  NO.sub.2                                                                          H  pyrazolyl-5                                                   308  H  H  NO.sub.2                                                                          H  4-chloropyrazolyl-5                                           309  H  H  NO.sub.2                                                                          H  1-methylpyrazolyl-5                                           310  H  H  NO.sub.2                                                                          H  1,2,3-thiadiazolyl-5                                          311  H  H  NO.sub.2                                                                          H  1,2,3-oxadiazolyl-5                                           312  H  H  NO.sub.2                                                                          H  1,2,3-oxadiazolyl-4                                           313  H  H  NO.sub.2                                                                          H  5-methyl-1,2,3-oxadiazolyl-4                                  314  H  H  NO.sub.2                                                                          H  4-methyl-1,2,3-oxadiazolyl-5                                  315  H  H  NO.sub.2                                                                          H  1,3,4-thiadiazolyl-2                                          316  H  H  NO.sub.2                                                                          H  2-methyl-1,3,4-thiadiazolyl-5                                 317  H  H  NO.sub.2                                                                          H  1,2,4-thiadiazolyl-3                                          318  H  H  NO.sub.2                                                                          H  1,2,4-thiadiazolyl-5                                          319  H  H  NO.sub.2                                                                          H  3-methyl-1,2,4-thiadiazolyl-5                                 320  H  H  NO.sub.2                                                                          H  1,2,4-oxadiazolyl-3                                           321  H  H  NO.sub.2                                                                          H  1,2,4-oxadiazolyl-5                                           322  H  H  NO.sub.2                                                                          H  1,2,4-triazolyl-5                                             323  H  H  NO.sub.2                                                                          H  1,2,4-triazolyl-3                                             324  H  H  NO.sub.2                                                                          H  1,3,4-oxadiazolyl-5                                           325  H  H  NO.sub.2                                                                          H  2-methyl-1,3,4-oxadiazolyl-5                                  326  H  H  NO.sub.2                                                                          H  2-chloro-1,3,4-oxadiazolyl-5                                  327  H  H  NO.sub.2                                                                          H  1,2,5-oxadiazolyl-3                                           328  H  H  NO.sub.2                                                                          H  3-methyl-1,2,5-oxadiazolyl-4                                  329  H  H  NO.sub.2                                                                          H  1,2,5-thiadiazolyl-3                                          330  H  H  NO.sub.2                                                                          H  3-methyl-1,2,5-thiadiazolyl-4                                 331  H  H  NO.sub.2                                                                          H  2-methylfuryl-5                                               332  H  H  NO.sub.2                                                                          H  2,5-dimethylfuryl                                                                             158-160                                        333  H  H  NO.sub.2                                                                          H  5-methyloxazolyl-4                                            334  H  H  NO.sub.2                                                                          H  4-methyloxazolyl-2                                            335  H  H  NO.sub.2                                                                          H  2-bromofuryl-5                                                336  H  H  NO.sub.2                                                                          H  2-methylfuryl-4                                               337  H  H  NO.sub.2                                                                          H  5-methylisoxazolyl-3                                          338  H  H  NO.sub.2                                                                          H  4-methylisoxazolyl-3                                          339  H  H  NO.sub.2                                                                          H  5-methylisothiazolyl-3                                        340  H  H  NO.sub.2                                                                          H  4-methylisothiazolyl-3                                        341  H  H  NO.sub.2                                                                          H  5-methyl-1,2,3-thiadiazolyl-4                                 342  H  H  NO.sub.2                                                                          H  4-methyl-1,2,3-thiadiazolyl-5                                                                 145-147                                        343  H  H  NO.sub.2                                                                          H  pyrryl-1                                                      344  H  H  NO.sub.2                                                                          H  imidazolyl-1                                                  345  H  H  NO.sub.2                                                                          H  pyrazolyl-1                                                   346  H  H  NO.sub.2                                                                          H  1,3,4-triazolyl-1                                             347  H  H  NO.sub.2                                                                          H  1,2,4-triazolyl-1                                             348  H  H  NO.sub.2                                                                          Cl thenyl-2                                                      349  H  H  NO.sub.2                                                                          Cl thenyl-3                                                      350  H  H  NO.sub.2                                                                          Cl 2-chlorothenyl-3                                              351  H  H  NO.sub.2                                                                          Cl 5-chlorothenyl-2                                              352  H  H  NO.sub.2                                                                          Cl 5-nitrothenyl-2                                               353  H  H  NO.sub.2                                                                          Cl 4-methylthenyl-2                                              354  H  H  NO.sub.2                                                                          Cl 3-methylthenyl-2                                              355  H  H  NO.sub.2                                                                          Cl 2-methylthenyl-3                                              356  H  H  NO.sub.2                                                                          Cl 3-methylthenyl-4                                              357  H  H  NO.sub.2                                                                          Cl 2,5-dimethylthenyl-4                                          358  H  H  NO.sub.2                                                                          Cl 2,3-dichlorothenyl-4                                          359  H  H  NO.sub.2                                                                          Cl 5-methylthenyl-2                                              360  H  H  NO.sub.2                                                                          Cl pyrryl-2                                                      361  H  H  NO.sub.2                                                                          Cl pyrryl-3                                                      362  H  H  NO.sub.2                                                                          Cl 3-methylpyrryl-2                                              363  H  H  NO.sub.2                                                                          Cl 2-methylpyrryl-3                                              364  H  H  NO.sub.2                                                                          Cl 5-chloropyrryl-2                                              365  H  H  NO.sub.2                                                                          Cl oxazolyl-2                                                    366  H  H  NO.sub.2                                                                          Cl oxazolyl-4                                                    367  H  H  NO.sub.2                                                                          Cl oxazolyl-5                                                    368  H  H  NO.sub.2                                                                          Cl 1,2,3-thiadiazolyl-4                                                                          205-207                                        369  H  H  NO.sub.2                                                                          Cl 4-methyloxazolyl-5                                            370  H  H  NO.sub.2                                                                          Cl 2-methyloxazolyl-5                                            371  H  H  NO.sub.2                                                                          Cl thiazolyl-2                                                   372  H  H  NO.sub.2                                                                          Cl thiazolyl-4                                                   373  H  H  NO.sub.2                                                                          Cl thiazolyl-5                                                   374  H  H  NO.sub.2                                                                          Cl 4-methylthiazolyl-5                                           375  H  H  NO.sub.2                                                                          Cl 2-methylthiazolyl-5                                           376  H  H  NO.sub.2                                                                          Cl imidazolyl-4                                                  377  H  H  NO.sub.2                                                                          Cl imidazolyl-5                                                  378  H  H  NO.sub.2                                                                          Cl 4-methylimidazolyl-5                                          379  H  H  NO.sub.2                                                                          Cl 1-methylimidazolyl-5                                          380  H  H  NO.sub.2                                                                          Cl 4-nitroimidazolyl-1                                           381  H  H  NO.sub.2                                                                          Cl 2-methyl-4-nitroimidazolyl-1                                  382  H  H  NO.sub.2                                                                          Cl 4,5-dichloroimidazolyl-1                                      383  H  H  NO.sub.2                                                                          Cl 1-methylpyrryl-2                                              384  H  H  NO.sub.2                                                                          Cl isoxazolyl-3   132-134                                        385  H  H  NO.sub.2                                                                          Cl isoxazolyl-4                                                  386  H  H  NO.sub.2                                                                          Cl 5-chloromethylisoxazolyl-3                                                                    138-141                                        387  H  H  NO.sub.2                                                                          Cl isothiazolyl-3                                                388  H  H  NO.sub.2                                                                          Cl isothiazolyl-4                                                389  H  H  NO.sub.2                                                                          Cl isothiazolyl-5                                                390  H  H  NO.sub.2                                                                          Cl 4-methylisothiazolyl-5                                        391  H  H  NO.sub.2                                                                          Cl pyrazolyl-4                                                   392  H  H  NO.sub.2                                                                          Cl pyrazolyl-5                                                   393  H  H  NO.sub.2                                                                          Cl 4-chloropyrazolyl-5                                           394  H  H  NO.sub.2                                                                          Cl 1-methylpyrazolyl-5                                           395  H  H  NO.sub.2                                                                          Cl 1,2,3-thiadiazolyl-5                                          396  H  H  NO.sub.2                                                                          Cl 1,2,3-oxadiazolyl-5                                           397  H  H  NO.sub.2                                                                          Cl 1,2,3-oxadiazolyl-4                                           398  H  H  NO.sub.2                                                                          Cl 5-methyl-1,2,3-oxadiazolyl-4                                  399  H  H  NO.sub.2                                                                          Cl 4-methyl-1,2,3-oxadiazolyl-5                                  400  H  H  NO.sub.2                                                                          Cl 1,3,4-thiadiazolyl-2                                          401  H  H  NO.sub.2                                                                          Cl 2-methyl-1,3,4-thiadiazolyl-5                                 402  H  H  NO.sub.2                                                                          Cl 1,2,4-thiadiazolyl-3                                          403  H  H  NO.sub.2                                                                          Cl 1,2,4-thiadiazolyl-5                                          404  H  H  NO.sub.2                                                                          Cl 3-methyl-1,2,4-thiadiazolyl-5                                 405  H  H  NO.sub.2                                                                          Cl 1,2,4-oxadiazolyl-3                                           406  H  H  NO.sub.2                                                                          Cl 1,2,4-oxadiazolyl-5                                           407  H  H  NO.sub.2                                                                          Cl 1,2,4-triazolyl-5                                             408  H  H  NO.sub.2                                                                          Cl 1,2,4-triazolyl-3                                             409  H  H  NO.sub.2                                                                          Cl 1,3,4-oxadiazolyl-5                                           410  H  H  NO.sub.2                                                                          Cl 2-methyl-1,3,4-oxadiazolyl-5                                  411  H  H  NO.sub.2                                                                          Cl 2-chloro-1,3,4-oxadiazolyl-5                                  412  H  H  NO.sub.2                                                                          Cl 1,2,5-oxadiazolyl-3                                           413  H  H  NO.sub.2                                                                          Cl 3-methyl-1,2,5-oxadiazolyl-4                                  414  H  H  NO.sub.2                                                                          Cl 1,2,5-thiadiazolyl-3                                          415  H  H  NO.sub.2                                                                          Cl 3-methyl-1,2,5-thiadiazolyl-4                                 416  H  H  NO.sub.2                                                                          Cl 2-methylfuryl-5                                               417  H  H  NO.sub.2                                                                          Cl 2,5-dimethylfuryl                                                                             116-118                                        418  H  H  NO.sub.2                                                                          Cl 2-chloro-furyl-5                                              419  H  H  NO.sub.2                                                                          Cl 5-methyloxazolyl-4                                            420  H  H  NO.sub.2                                                                          Cl 4-methyloxazolyl-2                                            421  H  H  NO.sub.2                                                                          Cl 2-bromofuryl-5                                                422  H  H  NO.sub.2                                                                          Cl 2-methylfuryl-4                                               423  H  H  NO.sub.2                                                                          Cl 5-methylisoxazolyl-3                                          424  H  H  NO.sub.2                                                                          Cl 4-methylisoxazolyl-3                                          425  H  H  NO.sub.2                                                                          Cl 5-methylisothiazolyl-3                                        426  H  H  NO.sub.2                                                                          Cl 4-methylisothiazolyl-3                                        427  H  H  NO.sub.2                                                                          Cl 4-methyl-1,2,3-thiadiazolyl-5                                                                 230-234                                        428  H  H  NO.sub.2                                                                          Cl 5-methyl-1,2,3-thiadiazolyl-4                                                                 145-148                                        429  H  H  NO.sub.2                                                                          Cl pyrryl-1                                                      430  H  H  NO.sub.2                                                                          Cl imidazolyl-1                                                  431  H  H  NO.sub.2                                                                          Cl pyrazolyl-1                                                   432  H  H  NO.sub.2                                                                          Cl 1,3,4-triazolyl-1                                             433  H  H  NO.sub.2                                                                          Cl 1,2,4-triazolyl-1                                             434  H  H  NO.sub.2                                                                          Br thenyl-2                                                      435  H  H  NO.sub.2                                                                          Br thenyl-3                                                      436  H  H  NO.sub.2                                                                          Br 2-chlorothenyl-3                                              437  H  H  NO.sub.2                                                                          Br 5-chlorothenyl-2                                              438  H  H  NO.sub.2                                                                          Br 5-nitrothenyl-2                                               439  H  H  NO.sub.2                                                                          Br 4-methylthenyl-2                                              440  H  H  NO.sub.2                                                                          Br 3-methylthenyl-2                                              441  H  H  NO.sub.2                                                                          Br 2-methylthenyl-3                                              442  H  H  NO.sub.2                                                                          Br 3-methylthenyl-4                                              443  H  H  NO.sub.2                                                                          Br 2,5-dimethylthenyl-4                                          444  H  H  NO.sub.2                                                                          Br 2,3-dichlorothenyl-4                                          445  H  H  NO.sub.2                                                                          Br 5-methylthenyl-2                                              446  H  H  NO.sub.2                                                                          Br pyrryl-2                                                      447  H  H  NO.sub.2                                                                          Br pyrryl-3                                                      448  H  H  NO.sub.2                                                                          Br 3-methylpyrryl-2                                              449  H  H  NO.sub.2                                                                          Br 2-methylpyrryl-3                                              450  H  H  NO.sub.2                                                                          Br 5-chloropyrryl-2                                              451  H  H  NO.sub.2                                                                          Br oxazolyl-2                                                    452  H  H  NO.sub.2                                                                          Br oxazolyl-4                                                    453  H  H  NO.sub.2                                                                          Br oxazolyl-5                                                    454  H  H  NO.sub.2                                                                          Br 4-methyloxazolyl-5                                            455  H  H  NO.sub.2                                                                          Br 2-methyloxazolyl-5                                            456  H  H  NO.sub.2                                                                          Br thiazolyl-2                                                   457  H  H  NO.sub.2                                                                          Br thiazolyl-4                                                   458  H  H  NO.sub.2                                                                          Br thiazolyl-5                                                   459  H  H  NO.sub.2                                                                          Br 4-methylthiazolyl-5                                           460  H  H  NO.sub.2                                                                          Br 2-methylthiazolyl-5                                           461  H  H  NO.sub.2                                                                          Br imidazolyl-4                                                  462  H  H  NO.sub.2                                                                          Br imidazolyl-5                                                  463  H  H  NO.sub.2                                                                          Br 4-methylimidazolyl-5                                          464  H  H  NO.sub.2                                                                          Br 1-methylimidazolyl-5                                          465  H  H  NO.sub.2                                                                          Br 4-nitroimidazolyl-1                                           466  H  H  NO.sub.2                                                                          Br 2-methyl-4-nitroimidazolyl-1                                  467  H  H  NO.sub.2                                                                          Br 4,5-dichloroimidazolyl-1                                      468  H  H  NO.sub.2                                                                          Br 1-methylpyrryl-2                                              469  H  H  NO.sub.2                                                                          Br isoxazolyl-3   143-147                                        470  H  H  NO.sub.2                                                                          Br isoxazolyl-4                                                  471  H  H  NO.sub.2                                                                          Br isoxazolyl-5   138-141                                        472  H  H  NO.sub.2                                                                          Br 5-chloromethyl-isoxazolyl-3                                   473  H  H  NO.sub.2                                                                          Br isothiazolyl-3                                                474  H  H  NO.sub.2                                                                          Br isothiazolyl-4                                                475  H  H  NO.sub.2                                                                          Br isothiazolyl-5                                                476  H  H  NO.sub.2                                                                          Br 4-methylisothiazolyl-5                                        477  H  H  NO.sub.2                                                                          Br pyrazolyl-4                                                   478  H  H  NO.sub.2                                                                          Br pyrazolyl-5                                                   479  H  H  NO.sub.2                                                                          Br 4-chloropyrazolyl-5                                           480  H  H  NO.sub.2                                                                          Br 1-methylpyrazolyl-5                                           481  H  H  NO.sub.2                                                                          Br 1,2,3-thiadiazolyl-5                                          482  H  H  NO.sub.2                                                                          Br 1,2,3-oxadiazolyl-5                                           483  H  H  NO.sub.2                                                                          Br 1,2,3-oxadiazolyl-4                                           484  H  H  NO.sub.2                                                                          Br 5-methyl-1,2,3-oxadiazolyl-4                                  485  H  H  NO.sub.2                                                                          Br 4-methyl-1,2,3-oxadiazolyl-5                                  486  H  H  NO.sub.2                                                                          Br 1,3,4-thiadiazolyl-2                                          487  H  H  NO.sub.2                                                                          Br 2-methyl-1,3,4-thiadiazolyl-5                                 488  H  H  NO.sub.2                                                                          Br 1,2,4-thiadiazolyl-3                                          489  H  H  NO.sub.2                                                                          Br 1,2,4-thiadiazolyl-5                                          490  H  H  NO.sub.2                                                                          Br 3-methyl-1,2,4-thiadiazolyl-5                                 491  H  H  NO.sub.2                                                                          Br 1,2,4-oxadiazolyl-3                                           492  H  H  NO.sub.2                                                                          Br 1,2,4-oxadiazolyl-5                                           493  H  H  NO.sub.2                                                                          Br 1,2,4-triazolyl-5                                             494  H  H  NO.sub.2                                                                          Br 1,2,4-triazolyl-3                                             495  H  H  NO.sub.2                                                                          Br 1,3,4-oxadiazolyl-5                                           496  H  H  NO.sub.2                                                                          Br 2-methyl-1,3,4-oxadiazolyl-5                                  497  H  H  NO.sub.2                                                                          Br 2-chloro-1,3,4-oxadiazolyl-5                                  498  H  H  NO.sub.2                                                                          Br 1,2,5-oxadiazolyl-3                                           499  H  H  NO.sub.2                                                                          Br 3-methyl-1,2,5-oxadiazolyl-4                                  500  H  H  NO.sub.2                                                                          Br 1,2,5-thiadiazolyl-3                                          501  H  H  NO.sub.2                                                                          Br 3-methyl-1,2,5-thiadiazolyl-4                                 502  H  H  NO.sub.2                                                                          Br 2-methylfuryl-5                                               503  H  H  NO.sub.2                                                                          Br 2,5-dimethylfuryl                                                                             121-123                                        504  H  H  NO.sub.2                                                                          Br 2-chlorofuryl-5                                               505  H  H  NO.sub.2                                                                          Br 5-methyloxazolyl-4                                            506  H  H  NO.sub.2                                                                          Br 4-methyloxazolyl-2                                            507  H  H  NO.sub.2                                                                          Br 2-bromofuryl-5                                                508  H  H  NO.sub.2                                                                          Br 2-methylfuryl-4                                               509  H  H  NO.sub.2                                                                          Br 5-methylisoxazolyl-3                                          510  H  H  NO.sub.2                                                                          Br 4-methylisoxazolyl-3                                          511  H  H  NO.sub.2                                                                          Br 5-methylisothiazolyl-3                                        512  H  H  NO.sub.2                                                                          Br 4-methylisothiazolyl-3                                        513  H  H  NO.sub.2                                                                          Br 4-methyl-1,2,3-thiadiazolyl-5                                 514  H  H  NO.sub.2                                                                          Br 5-methyl-1,2,3-thiadiazolyl-4                                 515  H  H  NO.sub.2                                                                          Br pyrryl-1                                                      516  H  H  NO.sub.2                                                                          Br imidazolyl-1                                                  517  H  H  NO.sub.2                                                                          Br pyrazolyl-1                                                   518  H  H  NO.sub.2                                                                          Br 1,3,4-triazolyl-1                                             519  H  H  NO.sub.2                                                                          Br 1,2,4-triazolyl-1                                             520  H  H  NO.sub.2                                                                          I  thenyl-2                                                      521  H  H  NO.sub.2                                                                          I  thenyl-3                                                      522  H  H  NO.sub.2                                                                          I  2-chlorothenyl-3                                              523  H  H  NO.sub.2                                                                          I  5-chlorothenyl-2                                              524  H  H  NO.sub.2                                                                          I  5-nitrothenyl-2                                               525  H  H  NO.sub.2                                                                          I  4-methylthenyl-2                                              526  H  H  NO.sub.2                                                                          I  3-methylthenyl-2                                              527  H  H  NO.sub.2                                                                          I  2-methylthenyl-3                                              528  H  H  NO.sub.2                                                                          I  3-methylthenyl-4                                              529  H  H  NO.sub. 2                                                                         I  2,5-dimethylthenyl-4                                          530  H  H  NO.sub.2                                                                          I  2,3-dichlorothenyl-4                                          531  H  H  NO.sub.2                                                                          I  5-methylthenyl-2                                              532  H  H  NO.sub.2                                                                          I  pyrryl-2                                                      533  H  H  NO.sub.2                                                                          I  pyrryl-3                                                      534  H  H  NO.sub.2                                                                          I  3-methylpyrryl-2                                              535  H  H  NO.sub.2                                                                          I  2-methylpyrryl-3                                              536  H  H  NO.sub.2                                                                          I  5-chloropyrryl-2                                              537  H  H  NO.sub.2                                                                          I  oxazolyl-2                                                    538  H  H  NO.sub.2                                                                          I  oxazolyl-4                                                    539  H  H  NO.sub.2                                                                          I  oxazolyl-5                                                    540  H  H  NO.sub.2                                                                          I  1,2,3-thiadiazolyl-4                                          541  H  H  NO.sub.2                                                                          I  4-methyloxazolyl-5                                            542  H  H  NO.sub.2                                                                          I  2-methyloxazolyl-5                                            543  H  H  NO.sub.2                                                                          I  thiazolyl-2                                                   544  H  H  NO.sub.2                                                                          I  thiazolyl-4                                                   545  H  H  NO.sub.2                                                                          I  thiazolyl-5                                                   546  H  H  NO.sub.2                                                                          I  4-methylthiazolyl-5                                           547  H  H  NO.sub.2                                                                          I  2-methylthiazolyl-5                                           548  H  H  NO.sub.2                                                                          I  imidazolyl-4                                                  549  H  H  NO.sub.2                                                                          I  imidazolyl-5                                                  550  H  H  NO.sub.2                                                                          I  4-methylimidazolyl-5                                          551  H  H  NO.sub.2                                                                          I  1-methylimidazolyl-5                                          552  H  H  NO.sub.2                                                                          I  4-nitroimidazolyl-1                                           553  H  H  NO.sub.2                                                                          I  2-methyl-4-nitroimidazolyl-1                                  554  H  H  NO.sub.2                                                                          I  4,5-dichloroimidazolyl-1                                      555  H  H  NO.sub.2                                                                          I  1-methylpyrryl-2                                              556  H  H  NO.sub.2                                                                          I  isoxazolyl-3                                                  557  H  H  NO.sub.2                                                                          I  isoxazolyl-4                                                  558  H  H  NO.sub.2                                                                          I  isoxazolyl-5                                                  559  H  H  NO.sub.2                                                                          I  5-chloromethylisoxazolyl-3                                    560  H  H  NO.sub.2                                                                          I  isothiazolyl-3                                                561  H  H  NO.sub.2                                                                          I  isothiazolyl-4                                                562  H  H  NO.sub.2                                                                          I  isothiazolyl-5                                                563  H  H  NO.sub.2                                                                          I  4-methylisothiazolyl-5                                        564  H  H  NO.sub.2                                                                          I  pyrazolyl-4                                                   565  H  H  NO.sub.2                                                                          I  pyrazolyl-5                                                   566  H  H  NO.sub.2                                                                          I  4-chloropyrazolyl-5                                           567  H  H  NO.sub.2                                                                          I  1-methylpyrazolyl-5                                           568  H  H  NO.sub.2                                                                          I  1,2,3-thiadiazolyl-5                                          569  H  H  NO.sub.2                                                                          I  1,2,3-oxadiazolyl-5                                           570  H  H  NO.sub.2                                                                          I  1,2,3-oxadiazolyl-4                                           571  H  H  NO.sub.2                                                                          I  5-methyl-1,2,3-oxadiazolyl-4                                  572  H  H  NO.sub.2                                                                          I  4-methyl-1,2,3-oxadiazolyl-5                                  573  H  H  NO.sub.2                                                                          I  1,3,4-thiadiazolyl-2                                          574  H  H  NO.sub.2                                                                          I  2-methyl-1,3,4-thiadiazolyl-5                                 575  H  H  NO.sub.2                                                                          I  1,2,4-thiadiazolyl-3                                          576  H  H  NO.sub.2                                                                          I  1,2,4-thiadiazolyl-5                                          577  H  H  NO.sub.2                                                                          I  3-methyl-1,2,4-thiadiazolyl-5                                 578  H  H  NO.sub.2                                                                          I  1,2,4-oxadiazolyl-3                                           579  H  H  NO.sub.2                                                                          I  1,2,4-oxadiazolyl-5                                           580  H  H  NO.sub.2                                                                          I  1,2,4-triazolyl-5                                             581  H  H  NO.sub.2                                                                          I  1,2,4-triazolyl-3                                             582  H  H  NO.sub.2                                                                          I  1,3,4-oxadiazolyl-5                                           583  H  H  NO.sub.2                                                                          I  2-methyl-1,3,4-oxadiazolyl-5                                  584  H  H  NO.sub.2                                                                          I  2-chloro-1,3,4-oxadiazolyl-5                                  585  H  H  NO.sub.2                                                                          I  1,2,5-oxadiazolyl-3                                           586  H  H  NO.sub.2                                                                          I  3-methyl-1,2,5-oxadiazolyl-4                                  587  H  H  NO.sub.2                                                                          I  1,2,5-thiadiazolyl-3                                          588  H  H  NO.sub.2                                                                          I  3-methyl-1,2,5-thiadiazolyl-4                                 589  H  H  NO.sub.2                                                                          I  2-methylfuryl-5                                               590  H  H  NO.sub.2                                                                          I  2,5-dimethylfuryl-4                                           591  H  H  NO.sub.2                                                                          I  2-chlorofuryl-5                                               592  H  H  NO.sub.2                                                                          I  5-methyloxazolyl-4                                            593  H  H  NO.sub.2                                                                          I  4-methyloxazolyl-2                                            594  H  H  NO.sub.2                                                                          I  2-bromofuryl-5                                                595  H  H  NO.sub.2                                                                          I  2-methylfuryl-4                                               596  H  H  NO.sub.2                                                                          I  5-methylisoxazolyl-3                                          597  H  H  NO.sub.2                                                                          I  4-methylisoxazolyl-3                                          598  H  H  NO.sub.2                                                                          I  5-methylisothiazolyl-3                                        599  H  H  NO.sub.2                                                                          I  4-methylisothiazolyl-3                                        600  H  H  NO.sub.2                                                                          I  4-methyl-1,2,3-thiadiazolyl-5                                 601  H  H  NO.sub.2                                                                          I  5-methyl-1,2,3-thiadiazolyl-4                                 602  H  H  NO.sub.2                                                                          I  pyrryl-1                                                      603  H  H  NO.sub.2                                                                          I  imidazolyl-1                                                  604  H  H  NO.sub.2                                                                          I  pyrazolyl-1                                                   605  H  H  NO.sub.2                                                                          I  1,3,4-triazolyl-1                                             606  H  H  NO.sub.2                                                                          I  1,2,4-triazolyl-1                                             607  H  H  NO.sub.2                                                                          NO.sub.2                                                                          thenyl-2                                                      608  H  H  NO.sub.2                                                                          NO.sub.2                                                                          thenyl-3                                                      609  H  H  NO.sub.2                                                                          NO.sub.2                                                                          2-chlorothenyl-3                                              610  H  H  NO.sub.2                                                                          NO.sub.2                                                                          5-chlorothenyl-2                                              611  H  H  NO.sub.2                                                                          NO.sub.2                                                                          5-nitrothenyl-2                                               612  H  H  NO.sub.2                                                                          NO.sub.2                                                                          4-methylthenyl-2                                              613  H  H  NO.sub.2                                                                          NO.sub.2                                                                          3-methylthenyl-2                                              614  H  H  NO.sub.2                                                                          NO.sub.2                                                                          2-methylthenyl-3                                              615  H  H  NO.sub.2                                                                          NO.sub.2                                                                          3-methylthenyl-4                                              616  H  H  NO.sub.2                                                                          NO.sub.2                                                                          2,5-dimethylthenyl-4                                          617  H  H  NO.sub.2                                                                          NO.sub.2                                                                          2,3-dichlorothenyl-4                                          618  H  H  NO.sub.2                                                                          NO.sub.2                                                                          5-methylthenyl-2                                              619  H  H  NO.sub.2                                                                          NO.sub.2                                                                          pyrryl-2                                                      620  H  H  NO.sub.2                                                                          NO.sub.2                                                                          pyrryl-3                                                      621  H  H  NO.sub.2                                                                          NO.sub.2                                                                          3-methylpyrryl-2                                              622  H  H  NO.sub.2                                                                          NO.sub.2                                                                          2-methylpyrryl-3                                              623  H  H  NO.sub.2                                                                          NO.sub.2                                                                          5-chloropyrryl-2                                              624  H  H  NO.sub.2                                                                          NO.sub.2                                                                          oxazolyl-2                                                    625  H  H  NO.sub.2                                                                          NO.sub.2                                                                          oxazolyl-4                                                    626  H  H  NO.sub.2                                                                          NO.sub.2                                                                          oxazolyl-5                                                    627  H  H  NO.sub.2                                                                          NO.sub.2                                                                          1,2,3-thiadiazolyl-4                                                                          172-174                                        628  H  H  NO.sub.2                                                                          NO.sub.2                                                                          4-methyloxazolyl-5                                            629  H  H  NO.sub.2                                                                          NO.sub.2                                                                          2-methyloxazolyl-5                                            630  H  H  NO.sub.2                                                                          NO.sub.2                                                                          thiazolyl-2                                                   631  H  H  NO.sub.2                                                                          NO.sub.2                                                                          thiazolyl-4                                                   632  H  H  NO.sub.2                                                                          NO.sub.2                                                                          thiazolyl-5                                                   633  H  H  NO.sub.2                                                                          NO.sub.2                                                                          4-methylthiazolyl-5                                           634  H  H  NO.sub.2                                                                          NO.sub.2                                                                          2-methylthiazolyl-5                                           635  H  H  NO.sub.2                                                                          NO.sub.2                                                                          imidazolyl-4                                                  636  H  H  NO.sub.2                                                                          NO.sub.2                                                                          imidazolyl-5                                                  637  H  H  NO.sub.2                                                                          NO.sub.2                                                                          4-methylimidazolyl-5                                          638  H  H  NO.sub.2                                                                          NO.sub.2                                                                          1-methylimidazolyl-5                                          639  H  H  NO.sub.2                                                                          NO.sub.2                                                                          4-nitroimidazolyl-1                                           640  H  H  NO.sub.2                                                                          NO.sub.2                                                                          2-methyl-4-nitroimidazolyl-1                                  641  H  H  NO.sub.2                                                                          NO.sub.2                                                                          4,5-dichloroimidazolyl-1                                      642  H  H  NO.sub.2                                                                          NO.sub.2                                                                          1-methylpyrryl-2                                              643  H  H  NO.sub.2                                                                          NO.sub.2                                                                          isoxazolyl-3   171-174                                        644  H  H  NO.sub.2                                                                          NO.sub.2                                                                          isoxazolyl-4                                                  645  H  H  NO.sub.2                                                                          NO.sub.2                                                                          isoxazolyl-5                                                  646  H  H  NO.sub.2                                                                          NO.sub.2                                                                          5-chloromethylisoxazolyl-3                                    647  H  H  NO.sub.2                                                                          NO.sub.2                                                                          isothiazolyl-3                                                648  H  H  NO.sub.2                                                                          NO.sub.2                                                                          isothiazolyl-4                                                649  H  H  NO.sub.2                                                                          NO.sub.2                                                                          isothiazolyl-5                                                650  H  H  NO.sub.2                                                                          NO.sub.2                                                                          4-methylisothiazolyl-5                                        651  H  H  NO.sub.2                                                                          NO.sub.2                                                                          pyrazolyl-4                                                   652  H  H  NO.sub.2                                                                          NO.sub.2                                                                          pyrazolyl-5                                                   653  H  H  NO.sub.2                                                                          NO.sub.2                                                                          4-chloropyrazolyl-5                                           654  H  H  NO.sub.2                                                                          NO.sub.2                                                                          1-methylpyrazolyl-5                                           655  H  H  NO.sub.2                                                                          NO.sub.2                                                                          1,2,3-thiadiazolyl-5                                          656  H  H  NO.sub.2                                                                          NO.sub.2                                                                          1,2,3-oxadiazolyl-5                                           657  H  H  NO.sub.2                                                                          NO.sub.2                                                                          1,2,3-oxadiazolyl-4                                           658  H  H  NO.sub.2                                                                          NO.sub.2                                                                          5-methyl-1,2,3-oxadiazolyl-4                                  659  H  H  NO.sub.2                                                                          NO.sub.2                                                                          4-methyl-1,2,3-oxadiazolyl-5                                  660  H  H  NO.sub.2                                                                          NO.sub.2                                                                          1,3,4-thiadiazolyl-2                                          661  H  H  NO.sub.2                                                                          NO.sub.2                                                                          2-methyl-1,3,4-thiadiazolyl-5                                 662  H  H  NO.sub.2                                                                          NO.sub.2                                                                          1,2,4-thiadiazolyl-3                                          663  H  H  NO.sub.2                                                                          NO.sub. 2                                                                         1,2,4-thiadiazolyl-5                                          664  H  H  NO.sub.2                                                                          NO.sub.2                                                                          3-methyl-1,2,4-thiadiazolyl-5                                 665  H  H  NO.sub.2                                                                          NO.sub.2                                                                          1,2,4-oxadiazolyl-3                                           666  H  H  NO.sub.2                                                                          NO.sub.2                                                                          1,2,4-oxadiazolyl-5                                           667  H  H  NO.sub.2                                                                          NO.sub.2                                                                          1,2,4-triazolyl-5                                             668  H  H  NO.sub.2                                                                          NO.sub.2                                                                          1,2,4-triazolyl-3                                             669  H  H  NO.sub.2                                                                          NO.sub.2                                                                          1,3,4-oxadiazolyl-5                                           670  H  H  NO.sub.2                                                                          NO.sub.2                                                                          2-methyl-1,3,4-oxadiazolyl-5                                  671  H  H  NO.sub.2                                                                          NO.sub.2                                                                          2-chloro-1,3,4-oxadiazolyl-5                                  672  H  H  NO.sub.2                                                                          NO.sub.2                                                                          1,2,5-oxadiazolyl-3                                           673  H  H  NO.sub.2                                                                          NO.sub.2                                                                          3-methyl-1,2,5-oxadiazolyl-4                                  674  H  H  NO.sub.2                                                                          NO.sub.2                                                                          1,2,5-thiadiazolyl-3                                          675  H  H  NO.sub.2                                                                          NO.sub.2                                                                          3-methyl-1,2,5-thiadiazolyl-4                                 676  H  H  NO.sub.2                                                                          NO.sub.2                                                                          2-methylfuryl-5                                               677  H  H  NO.sub.2                                                                          NO.sub.2                                                                          2,5-dimethylfuryl                                                                             145-150                                        678  H  H  NO.sub.2                                                                          NO.sub.2                                                                          2-chlorofuryl-5                                               679  H  H  NO.sub.2                                                                          NO.sub.2                                                                          5-methyloxazolyl-4                                            680  H  H  NO.sub.2                                                                          NO.sub.2                                                                          4-methyloxazolyl-2                                            681  H  H  NO.sub.2                                                                          NO.sub.2                                                                          2-bromofuryl-5                                                682  H  H  NO.sub.2                                                                          NO.sub.2                                                                          2-methylfuryl-4                                               683  H  H  NO.sub.2                                                                          NO.sub.2                                                                          5-methylisoxazolyl-3                                          684  H  H  NO.sub.2                                                                          NO.sub.2                                                                          4-methylisoxazolyl-3                                          685  H  H  NO.sub.2                                                                          NO.sub.2                                                                          5-methylisothiazolyl-3                                        686  H  H  NO.sub.2                                                                          NO.sub.2                                                                          4-methylisothiazolyl-3                                        687  H  H  NO.sub.2                                                                          NO.sub.2                                                                          4-methyl-1,2,3-thiadiazolyl-5                                 688  H  H  NO.sub. 2                                                                         NO.sub.2                                                                          5-methyl-1,2,3-thiadiazolyl-4                                 689  H  H  NO.sub.2                                                                          NO.sub.2                                                                          pyrryl-1                                                      690  H  H  NO.sub.2                                                                          NO.sub.2                                                                          imidazolyl-1                                                  691  H  H  NO.sub.2                                                                          NO.sub.2                                                                          pyrazolyl-1                                                   692  H  H  NO.sub.2                                                                          NO.sub.2                                                                          1,3,4-triazolyl-1                                             693  H  H  NO.sub.2                                                                          NO.sub.2                                                                          1,2,4-triazolyl-1                                             694  H  H  Cl H  thenyl-2                                                      695  H  H  Cl H  thenyl-3                                                      696  H  H  Cl H  2-chlorothenyl-3                                              697  H  H  Cl H  5-chlorothenyl-2                                              698  H  H  Cl H  5-nitrothenyl-2                                               699  H  H  Cl H  4-methylthenyl-2                                              700  H  H  Cl H  3-methylthenyl-2                                              701  H  H  Cl H  2-methylthenyl-3                                              702  H  H  Cl H  3-methylthenyl-4                                              703  H  H  Cl H  2,5-dimethylthenyl-4                                          704  H  H  Cl H  2,3-dichlorothenyl-4                                          705  H  H  Cl H  5-methylthenyl-2                                              706  H  H  Cl H  pyrryl-2                                                      707  H  H  Cl H  pyrryl-3                                                      708  H  H  Cl H  3-methylpyrryl-2                                              709  H  H  Cl H  2-methylpyrryl-3                                              710  H  H  Cl H  5-chloropyrryl-2                                              711  H  H  Cl H  oxazolyl-2                                                    712  H  H  Cl H  oxazolyl-4                                                    713  H  H  Cl H  oxazolyl-5                                                    714  H  H  Cl H  4-methyloxazolyl-5                                            715  H  H  Cl H  2-methyloxazolyl-5                                            716  H  H  Cl H  thiazolyl-2                                                   717  H  H  Cl H  thiazolyl-4                                                   718  H  H  Cl H  thiazolyl-5                                                   719  H  H  Cl H  4-methylthiazolyl-5                                           720  H  H  Cl H  2-methylthiazolyl-5                                           721  H  H  Cl H  imidazolyl-4                                                  722  H  H  Cl H  imidazolyl-5                                                  723  H  H  Cl H  4-methylimidazolyl-5                                          724  H  H  Cl H  1-methylimidazolyl-5                                          725  H  H  Cl H  4-nitroimidazolyl-1                                           726  H  H  Cl H  2-methyl-4-nitroimidazolyl-1                                  727  H  H  Cl H  4,5-dichloroimidazolyl-1                                      728  H  H  Cl H  1-methylpyrryl-2                                              729  H  H  Cl H  isoxazolyl-3   135-137                                        730  H  H  Cl H  isoxazolyl-4                                                  731  H  H  Cl H  isoxazolyl-5   125-128                                        732  H  H  Cl H  5-chloromethylisoxazolyl-3                                                                    130-133                                        733  H  H  Cl H  isothiazolyl-3                                                734  H  H  Cl H  isothiazolyl-4                                                735  H  H  Cl H  isothiazolyl-5                                                736  H  H  Cl H  4-methylisothiazolyl-5                                        737  H  H  Cl H  pyrazolyl-4                                                   738  H  H  Cl H  pyrazolyl-5                                                   739  H  H  Cl H  4-chloropyrazolyl-5                                           740  H  H  Cl H  1-methylpyrazolyl-5                                           741  H  H  Cl H  1,2,3-thiadiazolyl-5                                          742  H  H  Cl H  1,2,3-oxadiazolyl-5                                           743  H  H  Cl H  1,2,3-oxadiazolyl-4                                           744  H  H  Cl H  5-methyl-1,2,3-oxadiazolyl-4                                  745  H  H  Cl H  4-methyl-1,2,3-oxadiazolyl-5                                  746  H  H  Cl H  1,3,4-thiadiazolyl-2                                          747  H  H  Cl H  2-methyl-1,3,4-thiadiazolyl-5                                 748  H  H  Cl H  1,2,4-thiadiazolyl-3                                          749  H  H  Cl H  1,2,4-thiadiazolyl-5                                          750  H  H  Cl H  3-methyl-1,2,4-thiadiazolyl-5                                 751  H  H  Cl H  1,2,4-oxadiazolyl-3                                           752  H  H  Cl H  1,2,4-oxadiazolyl-5                                           753  H  H  Cl H  1,2,4-triazolyl-5                                             754  H  H  Cl H  1,2,4-triazolyl-3                                             755  H  H  Cl H  1,3,4-oxadiazolyl-5                                           756  H  H  Cl H  2-methyl-1,3,4-oxadiazolyl-5                                  757  H  H  Cl H  2-chloro-1,3,4-oxadiazolyl-5                                  758  H  H  Cl H  1,2,5-oxadiazolyl-3                                           759  H  H  Cl H  3-methyl-1,2,5-oxadiazolyl-4                                  760  H  H  Cl H  1,2,5-thiadiazolyl-3                                          761  H  H  Cl H  3-methyl-1,2,5-thiadiazolyl-4                                 762  H  H  Cl H  2-methylfuryl-5                                               763  H  H  Cl H  2,5-dimethylfuryl-4                                                                           105-106                                        764  H  H  Cl H  2-chloro-furyl-5                                              765  H  H  Cl H  5-methyloxazolyl-4                                            766  H  H  Cl H  4-methyloxazolyl-2                                            767  H  H  Cl H  2-bromofuryl-5                                                768  H  H  Cl H  2-methylfuryl-4                                               769  H  H  Cl H  5-methylisoxazolyl-3                                          770  H  H  Cl H  4-methylisoxazolyl-3                                          771  H  H  Cl H  5-methylisothiazolyl-3                                        772  H  H  Cl H  4-methylisothiazolyl-3                                        773  H  H  Cl H  5-methyl-1,2,3-thiadiazolyl-4                                 774  H  H  Cl H  pyrryl-1                                                      775  H  H  Cl H  imidazolyl-1                                                  776  H  H  Cl H  pyrazolyl-1                                                   777  H  H  Cl H  1,3,4-triazolyl-1                                             778  H  H  Cl H  1,2,4-triazolyl-1                                             779  H  H  Cl NO.sub.2                                                                          thenyl-2                                                      780  H  H  Cl NO.sub.2                                                                          thenyl-3                                                      781  H  H  Cl NO.sub.2                                                                          2-chlorothenyl-3                                              782  H  H  Cl NO.sub.2                                                                          5-chlorothenyl-2                                              783  H  H  Cl NO.sub.2                                                                          5-nitrothenyl-2                                               784  H  H  Cl NO.sub.2                                                                          4-methylthenyl-2                                              785  H  H  Cl NO.sub.2                                                                          3-methylthenyl-2                                              786  H  H  Cl NO.sub.2                                                                          2-methylthenyl-3                                              787  H  H  Cl NO.sub.2                                                                          3-methylthenyl-4                                              788  H  H  Cl NO.sub.2                                                                          2,5-dimethylthenyl-4                                          789  H  H  Cl NO.sub.2                                                                          2,3-dichlorothenyl-4                                          790  H  H  Cl NO.sub.2                                                                          5-methylthenyl-2                                              791  H  H  Cl NO.sub.2                                                                          pyrryl-2                                                      792  H  H  Cl NO.sub.2                                                                          pyrryl-3                                                      793  H  H  Cl NO.sub.2                                                                          3-methylpyrryl-2                                              794  H  H  Cl NO.sub.2                                                                          2-methylpyrryl-3                                              795  H  H  Cl NO.sub.2                                                                          5-chloropyrryl-2                                              796  H  H  Cl NO.sub.2                                                                          oxazolyl-2                                                    797  H  H  Cl NO.sub.2                                                                          oxazolyl-4                                                    798  H  H  Cl NO.sub.2                                                                          oxazolyl-5                                                    799  H  H  Cl NO.sub.2                                                                          1,2,3-thiadiazolyl-4                                          800  H  H  Cl NO.sub.2                                                                          4-methyloxazolyl-5                                            801  H  H  Cl NO.sub.2                                                                          2-methyloxazolyl-5                                            802  H  H  Cl NO.sub.2                                                                          thiazolyl-2                                                   803  H  H  Cl NO.sub.2                                                                          thiazolyl-4                                                   804  H  H  Cl NO.sub.2                                                                          thiazolyl-5                                                   805  H  H  Cl NO.sub.2                                                                          4-methylthiazolyl-5                                           806  H  H  Cl NO.sub.2                                                                          2-methylthiazolyl-5                                           807  H  H  Cl NO.sub.2                                                                          imidazolyl-4                                                  808  H  H  Cl NO.sub.2                                                                          imidazolyl-5                                                  809  H  H  Cl NO.sub.2                                                                          4-methylimidazolyl-5                                          810  H  H  Cl NO.sub.2                                                                          1-methylimidazolyl-5                                          811  H  H  Cl NO.sub.2                                                                          4-nitroimidazolyl-5                                           812  H  H  Cl NO.sub.2                                                                          2-methyl-4-nitroimidazolyl-1                                  813  H  H  Cl NO.sub.2                                                                          4,5-dichloroimidazolyl-1                                      814  H  H  Cl NO.sub.2                                                                          1-methylpyrryl-2                                              815  H  H  Cl NO.sub.2                                                                          isoxazolyl-3   128-130                                        816  H  H  Cl NO.sub.2                                                                          isoxazolyl-4                                                  817  H  H  Cl NO.sub.2                                                                          isoxazolyl-5                                                  818  H  H  Cl NO.sub.2                                                                          5-chloromethylisoxazolyl-3                                                                    122-125                                        819  H  H  Cl NO.sub.2                                                                          isothiazolyl-3                                                820  H  H  Cl NO.sub.2                                                                          isothiazolyl-4                                                821  H  H  Cl NO.sub.2                                                                          isothiazolyl-5                                                822  H  H  Cl NO.sub.2                                                                          4-methylisothiazolyl-5                                        823  H  H  Cl NO.sub.2                                                                          pyrazolyl-4                                                   824  H  H  Cl NO.sub.2                                                                          pyrazolyl-5                                                   825  H  H  Cl NO.sub.2                                                                          4-chloropyrazolyl-5                                           826  H  H  Cl NO.sub.2                                                                          1-methylpyrazolyl-5                                           827  H  H  Cl NO.sub.2                                                                          1,2,3-thiadiazolyl-5                                          828  H  H  Cl NO.sub.2                                                                          1,2,3-oxadiazolyl-5                                           829  H  H  Cl NO.sub.2                                                                          1,2,3-oxadiazolyl-4                                           830  H  H  Cl NO.sub.2                                                                          5-methyl-1,2,3-oxadiazolyl-4                                  831  H  H  Cl NO.sub.2                                                                          4-methyl-1,2,3-oxadiazolyl-5                                  832  H  H  Cl NO.sub.2                                                                          1,3,4-thiadiazolyl-2                                          833  H  H  Cl NO.sub.2                                                                          2-methyl-1,3,4-thiadiazolyl-5                                 834  H  H  Cl NO.sub.2                                                                          1,2,4-thiadiazolyl-3                                          835  H  H  Cl NO.sub.2                                                                          1,2,4-thiadiazolyl-5                                          836  H  H  Cl NO.sub.2                                                                          3-methyl-1,2,4-thiadiazolyl-5                                 837  H  H  Cl NO.sub.2                                                                          1,2,4-oxadiazolyl-3                                           838  H  H  Cl NO.sub.2                                                                          1,2,4-oxadiazolyl-5                                           839  H  H  Cl NO.sub.2                                                                          1,2,4-triazolyl-5                                             840  H  H  Cl NO.sub.2                                                                          1,2,4-triazolyl-3                                             841  H  H  Cl NO.sub.2                                                                          1,3,4-oxadiazolyl-5                                           842  H  H  Cl NO.sub.2                                                                          2-methyl-1,3,4-oxadiazolyl-5                                  843  H  H  Cl NO.sub.2                                                                          2-chloro-1,3,4-oxadiazolyl-5                                  844  H  H  Cl NO.sub.2                                                                          1,2,5-oxadiazolyl-3                                           845  H  H  Cl NO.sub.2                                                                          3-methyl-1,2,5-oxadiazolyl-4                                  846  H  H  Cl NO.sub.2                                                                          1,2,5-thiadiazolyl-3                                          847  H  H  Cl NO.sub.2                                                                          3-methyl-1,2,5-thiadiazolyl-4                                 848  H  H  Cl NO.sub.2                                                                          2-methylfuryl-5                                               849  H  H  Cl NO.sub.2                                                                          2,5-dimethylfuryl-4                                                                           141-144                                        850  H  H  Cl NO.sub.2                                                                          2-chlorofuryl-5                                               851  H  H  Cl NO.sub.2                                                                          5-methyloxazolyl-4                                            852  H  H  Cl NO.sub.2                                                                          4-methyloxazolyl-2                                            853  H  H  Cl NO.sub.2                                                                          2-bromofuryl-5                                                854  H  H  Cl NO.sub.2                                                                          2-methylfuryl-4                                               855  H  H  Cl NO.sub.2                                                                          5-methylisoxazolyl-3                                          856  H  H  Cl NO.sub.2                                                                          4-methylisoxazolyl-3                                          857  H  H  Cl NO.sub.2                                                                          5-methylisothiazolyl-3                                        858  H  H  Cl NO.sub.2                                                                          4-methylisothiazolyl-3                                        859  H  H  Cl NO.sub.2                                                                          4-methyl-1,2,3-thiadiazolyl-5                                                                 137-138                                        860  H  H  Cl NO.sub.2                                                                          5-methyl-1,2,3-thiadiazolyl-4                                 861  H  H  Cl NO.sub.2                                                                          pyrryl-1                                                      862  H  H  Cl NO.sub.2                                                                          imidazolyl-1                                                  863  H  H  Cl NO.sub.2                                                                          pyrazolyl-1                                                   864  H  H  Cl NO.sub.2                                                                          1,3,4-triazolyl-1                                             865  H  H  Cl NO.sub.2                                                                          1,2,4-triazolyl-1                                             866  H  H  Br NO.sub.2                                                                          thenyl-2                                                      867  H  H  Br NO.sub.2                                                                          thenyl-3                                                      868  H  H  Br NO.sub.2                                                                          2-chlorothenyl-3                                              869  H  H  Br NO.sub.2                                                                          5-chlorothenyl-2                                              870  H  H  Br NO.sub.2                                                                          5-nitrothenyl-2                                               871  H  H  Br NO.sub.2                                                                          4-methylthenyl-2                                              872  H  H  Br NO.sub.2                                                                          3-methylthenyl-2                                              873  H  H  Br NO.sub.2                                                                          2-methylthenyl-3                                              874  H  H  Br NO.sub.2                                                                          3-methylthenyl-4                                              875  H  H  Br NO.sub.2                                                                          2,5-dimethylthenyl-4                                          876  H  H  Br NO.sub.2                                                                          2,3-dichlorothenyl-4                                          877  H  H  Br NO.sub.2                                                                          5-methylthenyl-2                                              878  H  H  Br NO.sub.2                                                                          pyrryl-2                                                      879  H  H  Br NO.sub.2                                                                          pyrryl-3                                                      880  H  H  Br NO.sub.2                                                                          3-methylpyrryl-2                                              881  H  H  Br NO.sub.2                                                                          2-methylpyrryl-3                                              882  H  H  Br NO.sub.2                                                                          5-chloropyrryl-2                                              883  H  H  Br NO.sub.2                                                                          oxazolyl-2                                                    884  H  H  Br NO.sub.2                                                                          oxazolyl-4                                                    885  H  H  Br NO.sub.2                                                                          oxazolyl-5                                                    886  H  H  Br NO.sub.2                                                                          1,2,3-thiadiazolyl                                                                            172 (decomp.)                                  887  H  H  Br NO.sub.2                                                                          4-methyloxazolyl-5                                            888  H  H  Br NO.sub.2                                                                          2-methyloxazolyl-5                                            889  H  H  Br NO.sub.2                                                                          thiazolyl-2                                                   890  H  H  Br NO.sub.2                                                                          thiazolyl-4                                                   891  H  H  Br NO.sub.2                                                                          thiazolyl-5                                                   892  H  H  Br NO.sub.2                                                                          4-methylthiazolyl-5                                           893  H  H  Br NO.sub.2                                                                          2-methylthiazolyl-5                                           894  H  H  Br NO.sub.2                                                                          imidazolyl-4                                                  895  H  H  Br NO.sub.2                                                                          imidazolyl-5                                                  896  H  H  Br NO.sub.2                                                                          4-methylimidazolyl-5                                          897  H  H  Br NO.sub.2                                                                          1-methylimidazolyl-5                                          898  H  H  Br NO.sub.2                                                                          4-nitroimidazolyl-5                                           899  H  H  Br NO.sub.2                                                                          2-methyl-4-nitroimidazolyl-1                                  900  H  H  Br NO.sub.2                                                                          4,5-dichloroimidazolyl-1                                      901  H  H  Br NO.sub.2                                                                          1-methylpyrryl-2                                              902  H  H  Br NO.sub.2                                                                          isoxazolyl-3   159-162                                        903  H  H  Br NO.sub.2                                                                          isoxazolyl-4                                                  904  H  H  Br NO.sub.2                                                                          isoxazolyl-5   159-160                                        905  H  H  Br NO.sub.2                                                                          5-chloromethylisoxazolyl-3                                    906  H  H  Br NO.sub.2                                                                          isothiazolyl-3                                                907  H  H  Br NO.sub.2                                                                          isothiazolyl-4                                                908  H  H  Br NO.sub.2                                                                          isothiazolyl-5                                                909  H  H  Br NO.sub.2                                                                          4-methylisothiazolyl-5                                        910  H  H  Br NO.sub.2                                                                          pyrazolyl-4                                                   911  H  H  Br NO.sub.2                                                                          pyrazolyl-5                                                   912  H  H  Br NO.sub.2                                                                          4-chloropyrazolyl-5                                           913  H  H  Br NO.sub.2                                                                          1-methylpyrazolyl-5                                           914  H  H  Br NO.sub.2                                                                          1,2,3-thiadiazolyl-5                                          915  H  H  Br NO.sub.2                                                                          1,2,3-oxadiazolyl-5                                           916  H  H  Br NO.sub.2                                                                          1,2,3-oxadiazolyl-4                                           917  H  H  Br NO.sub.2                                                                          5-methyl-1,2,3-oxadiazolyl-4                                  918  H  H  Br NO.sub.2                                                                          4-methyl-1,2,3-oxadiazolyl-5                                  919  H  H  Br NO.sub.2                                                                          1,3,4-thiadiazolyl-2                                          920  H  H  Br NO.sub.2                                                                          2-methyl-1,3,4-thiadiazolyl-5                                 921  H  H  Br NO.sub.2                                                                          1,2,4-thiadiazolyl-3                                          922  H  H  Br NO.sub.2                                                                          1,2,4-thiadiazolyl-5                                          923  H  H  Br NO.sub.2                                                                          3-methyl-1,2,4-thiadiazolyl-5                                 924  H  H  Br NO.sub.2                                                                          1,2,4-oxadiazolyl-3                                           925  H  H  Br NO.sub.2                                                                          1,2,4-oxadiazolyl-5                                           926  H  H  Br NO.sub.2                                                                          1,2,4-triazolyl-5                                             927  H  H  Br NO.sub.2                                                                          1,2,4-triazolyl-3                                             928  H  H  Br NO.sub.2                                                                          1,3,4-oxadiazolyl-5                                           929  H  H  Br NO.sub.2                                                                          2-methyl-1,3,4-oxadiazolyl-5                                  930  H  H  Br NO.sub.2                                                                          2-chloro-1,3,4-oxadiazolyl-5                                  931  H  H  Br NO.sub.2                                                                          1,2,5-oxadiazolyl-3                                           932  H  H  Br NO.sub.2                                                                          3-methyl-1,2,5-oxadiazolyl-4                                  933  H  H  Br NO.sub.2                                                                          1,2,5-thiadiazolyl-3                                          934  H  H  Br NO.sub.2                                                                          3-methyl-1,2,5-thiadiazolyl-4                                 935  H  H  Br NO.sub.2                                                                          2-methylfuryl-5                                               936  H  H  Br NO.sub.2                                                                          2,5-dimethylfuryl-4                                                                           144-146                                        937  H  H  Br NO.sub.2                                                                          2-chlorofuryl-5                                               938  H  H  Br NO.sub.2                                                                          5-methyloxazolyl-4                                            939  H  H  Br NO.sub.2                                                                          4-methyloxazolyl-2                                            940  H  H  Br NO.sub.2                                                                          2-bromofuryl-5                                                941  H  H  Br NO.sub.2                                                                          2-methylfuryl-4                                               942  H  H  Br NO.sub.2                                                                          5-methylisoxazolyl-3                                          943  H  H  Br NO.sub.2                                                                          4-methylisoxazolyl-3                                          944  H  H  Br NO.sub.2                                                                          5-methylisothiazolyl-3                                        945  H  H  Br NO.sub.2                                                                          4-methylisothiazolyl-3                                        946  H  H  Br NO.sub.2                                                                          4-methyl-1,2,3-thiadiazolyl-5                                                                 148-150                                        947  H  H  Br NO.sub.2                                                                          5-methyl-1,2,3-thiadiazolyl-4                                 948  H  H  Br NO.sub.2                                                                          pyrryl-1                                                      949  H  H  Br NO.sub.2                                                                          imidazolyl-1                                                  950  H  H  Br NO.sub.2                                                                          pyrazolyl-1                                                   951  H  H  Br NO.sub.2                                                                          1,3,4-triazolyl-1                                             952  H  H  Br NO.sub.2                                                                          1,2,4-triazolyl-1                                             953  H  H  Br H  thenyl-2                                                      954  H  H  Br H  thenyl-3                                                      955  H  H  Br H  2-chlorothenyl-3                                              956  H  H  Br H  5-chlorothenyl-2                                              957  H  H  Br H  5-nitrothenyl-2                                               958  H  H  Br H  4-methylthenyl-2                                              959  H  H  Br H  3-methylthenyl-2                                              960  H  H  Br H  2-methylthenyl-3                                              961  H  H  Br H  3-methylthenyl-4                                              962  H  H  Br H  2,5-dimethylthenyl-4                                          963  H  H  Br H  2,3-dichlorothenyl-4                                          964  H  H  Br H  5-methylthenyl-2                                              965  H  H  Br H  pyrryl-2                                                      966  H  H  Br H  pyrryl-3                                                      967  H  H  Br H  3-methylpyrryl-2                                              968  H  H  Br H  2-methylpyrryl-3                                              969  H  H  Br H  5-chloropyrryl-2                                              970  H  H  Br H  oxazolyl-2                                                    971  H  H  Br H  oxazolyl-4                                                    972  H  H  Br H  oxazolyl-5                                                    973  H  H  Br H  1,2,3-thiadiazolyl-4                                                                          158-159                                        974  H  H  Br H  4-methyloxazolyl-5                                            975  H  H  Br H  2-methyloxazolyl-5                                            976  H  H  Br H  thiazolyl-2                                                   977  H  H  Br H  thiazolyl-4                                                   978  H  H  Br H  thiazolyl-5                                                   979  H  H  Br H  4-methylthiazolyl-5                                           980  H  H  Br H  2-methylthiazolyl-5                                           981  H  H  Br H  imidazolyl-4                                                  982  H  H  Br H  imidazolyl-5                                                  983  H  H  Br H  4-methylimidazolyl-5                                          984  H  H  Br H  1-methylimidazolyl-5                                          985  H  H  Br H  4-nitroimidazolyl-1                                           986  H  H  Br H  2-methyl-4-nitroimidazolyl-1                                  987  H  H  Br H  4,5-dichloroimidazolyl-1                                      988  H  H  Br H  1-methylpyrryl-2                                              989  H  H  Br H  isoxazolyl-3   128-129                                        990  H  H  Br H  isoxazolyl-4                                                  991  H  H  Br H  isoxazolyl-5   135-137                                        992  H  H  Br H  5-chloromethylisoxazolyl-3                                                                    134-136                                        993  H  H  Br H  isothiazolyl-3                                                994  H  H  Br H  isothiazolyl-4                                                995  H  H  Br H  isothiazolyl-5                                                996  H  H  Br H  4-methylisothiazolyl-5                                        997  H  H  Br H  pyrazolyl-4                                                   998  H  H  Br H  pyrazolyl-5                                                   999  H  H  Br H  4-chloropyrazolyl-5                                           1000 H  H  Br H  1-methylpyrazolyl-5                                           1001 H  H  Br H  1,2,3-thiadiazolyl-5                                          1002 H  H  Br H  1,2,3-oxadiazolyl-5                                           1003 H  H  Br H  1,2,3-oxadiazolyl-4                                           1004 H  H  Br H  5-methyl-1,2,3-oxadiazolyl-4                                  1005 H  H  Br H  4-methyl-1,2,3-oxadiazolyl-5                                  1006 H  H  Br H  1,3,4-thiadiazolyl-2                                          1007 H  H  Br H  2-methyl-1,3,4-thiadiazolyl-5                                 1008 H  H  Br H  1,2,4-thiadiazolyl-3                                          1009 H  H  Br H  1,2,4-thiadiazolyl-5                                          1010 H  H  Br H  3-methyl-1,2,4-thiadiazolyl-5                                 1011 H  H  Br H  1,2,4-oxadiazolyl-3                                           1012 H  H  Br H  1,2,4-oxadiazolyl-5                                           1013 H  H  Br H  1,2,4-triazolyl-5                                             1014 H  H  Br H  1,2,4-triazolyl-3                                             1015 H  H  Br H  1,3,4-oxadiazolyl-5                                           1016 H  H  Br H  2-methyl-1,3,4-oxadiazolyl-5                                  1017 H  H  Br H  2-chloro-1,3,4-oxadiazolyl-5                                  1018 H  H  Br H  1,2,5-oxadiazolyl-3                                           1019 H  H  Br H  3-methyl-1,2,5-oxadiazolyl-4                                  1020 H  H  Br H  1,2,5-thiadiazolyl-3                                          1021 H  H  Br H  3-methyl-1,2,5-thiadiazolyl-4                                 1022 H  H  Br H  2-methylfuryl-5                                               1023 H  H  Br H  2,5-dimethylfuryl-4                                                                           116-117                                        1024 H  H  Br H  2-chlorofuryl-5                                               1025 H  H  Br H  5-methyloxazolyl-4                                            1026 H  H  Br H  4-methyloxazolyl-2                                            1027 H  H  Br H  2-bromofuryl-5                                                1028 H  H  Br H  2-methylfuryl-4                                               1029 H  H  Br H  5-methylisoxazolyl-3                                          1030 H  H  Br H  4-methylisoxazolyl-3                                          1031 H  H  Br H  5-methylisothiazolyl-3                                        1032 H  H  Br H  4-methylisothiazolyl-3                                        1033 H  H  Br H  4-methyl-1,2,3-thiadiazolyl-5                                                                 120-121                                        1034 H  H  Br H  5-methyl-1,2,3-thiadiazolyl-4                                 1035 H  H  Br H  pyrryl-1                                                      1036 H  H  Br H  imidazolyl-1                                                  1037 H  H  Br H  pyrazolyl-1                                                   1038 H  H  Br H  1,3,4-triazolyl-1                                             1039 H  H  Br H  1,2,4-triazolyl-1                                             1040 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          thenyl-2                                                      1041 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          thenyl-3                                                      1042 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          2,5-dimethylthenyl-4                                          1043 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          5-methylthenyl-2                                              1044 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          pyrryl-2                                                      1045 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          pyrryl-3                                                      1046 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          oxazolyl-2                                                    1047 CH.sub.3                                                                          H  NO.sub. 2                                                                         NO.sub.2                                                                          oxazolyl-4                                                    1048 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          oxazolyl-5                                                    1049 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          1,2,3-thiadiazolyl-4                                          1050 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          4-methyloxazolyl-5                                            1051 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          thiazolyl-2                                                   1052 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          thiazolyl-4                                                   1053 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          thiazolyl-5                                                   1054 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          4-methylthiazolyl-5                                           1055 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          imidazolyl-4                                                  1056 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          imidazolyl-5                                                  1057 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          4-methylimidazolyl-5                                          1058 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          1-methylimidazolyl-5                                          1059 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          4-nitroimidazolyl-1                                           1060 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          2-methyl-4-nitroimidazolyl-1                                  1061 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          4,5-dichloroimidazolyl-1                                      1062 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          1-methylpyrryl-2                                              1063 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          isoxazolyl-3                                                  1064 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          isoxazolyl-4                                                  1065 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          isoxazolyl-5                                                  1066 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          5-chloromethylisoxazolyl-3                                    1067 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          isothiazolyl-3                                                1068 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          isothiazolyl-4                                                1069 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub. 2                                                                         isothiazolyl-5                                                1070 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          4-methylisothiazolyl-5                                        1071 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          pyrazolyl-4                                                   1072 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          pyrazolyl-5                                                   1073 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          1-methylpyrazolyl-5                                           1074 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          1,2,3-thiadiazolyl-5                                          1075 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          1,2,3-oxadiazolyl-5                                           1076 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          1,2,3-oxadiazolyl-4                                           1077 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          5-methyl-1,2,3-oxadiazolyl-4                                  1078 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          4-methyl-1,2,3-oxadiazolyl-5                                  1079 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          1,3,4-thiadiazolyl-2                                          1080 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          2-methyl-1,3,4-thiadiazolyl-5                                 1081 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          1,2,4-thiadiazolyl-3                                          1082 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          1,2,4-thiadiazolyl-5                                          1083 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          3-methyl-1,2,4-thiadiazolyl-5                                 1084 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          1,2,4-oxadiazolyl-3                                           1085 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          1,2,4-oxadiazolyl-5                                           1086 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          1,2,4-triazolyl-5                                             1087 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          1,2,4-triazolyl-3                                             1088 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          1,3,4-oxadiazolyl-5                                           1089 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          2-methyl-1,3,4-oxadiazolyl-5                                  1090 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          1,2,5-oxadiazolyl-3                                           1091 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          3-methyl-1,2,5-oxadiazolyl-4                                  1092 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          1,2,5-thiadiazolyl-3                                          1093 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          3-methyl-1,2,5-thiadiazolyl-4                                 1094 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          2-methylfuryl-5                                               1095 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          2,5-dimethylfuryl-4                                                                           156-160                                        1096 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          2-chlorofuryl-5                                               1097 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          5-methyloxazolyl-4                                            1098 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          4-methyloxazolyl-2                                            1099 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          5-methylisoxazolyl-3                                          1100 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          4-methylisoxazolyl-3                                          1101 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          5-methylisothiazolyl-3                                        1102 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          4-methylisothiazolyl-3                                        1103 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          4-methyl-1,2,3-thiadiazolyl-5                                 1104 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          5-methyl-1,2,3-thiadiazolyl-4                                 1105 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          pyrryl-1                                                      1106 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          imidazolyl-1                                                  1107 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          pyrazolyl-1                                                   1108 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          1,3,4-triazolyl-1                                             1109 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          1,2,4-triazolyl-1                                             1110 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl thenyl-2                                                      1111 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl thenyl-3                                                      1112 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 2,5-dimethylthenyl-4                                          1113 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 5-methylthenyl-2                                              1114 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl pyrryl-2                                                      1115 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl pyrryl-3                                                      1116 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl oxazolyl-2                                                    1117 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl oxazolyl-4                                                    1118 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl oxazolyl-5                                                    1119 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 1,2,3-thiadiazolyl-4                                          1120 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 4-methyloxazolyl-5                                            1121 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl thiazolyl-2                                                   1122 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl thiazolyl-4                                                   1123 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl thiazolyl-5                                                   1124 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 4-methylthiazolyl-5                                           1125 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl imidazolyl-4                                                  1126 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl imidazolyl-5                                                  1127 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 4-methylimidazolyl-5                                          1128 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 1-methylimidazolyl-5                                          1129 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 4-nitroimidazolyl-1                                           1130 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 2-methyl-4-nitroimidazolyl-1                                  1131 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 4,5-dichloroimidazolyl-1                                      1132 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 1-methylpyrryl-2                                              1133 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl isoxazolyl-3                                                  1134 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl isoxazolyl-4                                                  1135 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl isoxazolyl-5                                                  1136 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 5-chloromethylisoxazolyl-3                                    1137 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl isothiazolyl-3                                                1138 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl isothiazolyl-4                                                1139 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl isothiazolyl-5                                                1140 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 4-methylisothiazolyl-5                                        1141 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl pyrazolyl-4                                                   1142 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl pyrazolyl-5                                                   1143 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 1-methylpyrazolyl-5                                           1144 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 1,2,3-thiadiazolyl-5                                          1145 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 1,2,3-oxadiazolyl-5                                           1146 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 1,2,3-oxadiazolyl-4                                           1147 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 5-methyl-1,2,3-oxadiazolyl-4                                  1148 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 4-methyl-1,2,3-oxadiazolyl-5                                  1149 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 1,3,4-thiadiazolyl-2                                          1150 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 2-methyl-1,3,4-thiadiazolyl-5                                 1151 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 1,2,4-thiadiazolyl-3                                          1152 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 1,2,4-thiadiazolyl-5                                          1153 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 3-methyl-1,2,4-thiadiazolyl-5                                 1154 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 1,2,4-oxadiazolyl-3                                           1155 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 1,2,4-oxadiazolyl-5                                           1156 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 1,2,4-triazolyl-5                                             1157 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 1,2,4-triazolyl-3                                             1158 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 1,3,4-oxadiazolyl-5                                           1159 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 2-methyl-1,3,4-oxadiazolyl-5                                  1160 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 1,2,5-oxadiazolyl-3                                           1161 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 3-methyl-1,2,5-oxadiazolyl-4                                  1162 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 1,2,5-thiadiazolyl-3                                          1163 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 3-methyl-1,2,5-thiadiazolyl-4                                 1164 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 2-methylfuryl-5                                               1165 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 2,5-dimethylfuryl-4                                           1166 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 2-chlorofuryl-5                                               1167 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 5-methyloxazolyl-4                                            1168 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 4-methyloxazolyl-2                                            1169 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 5-methylisoxazolyl-3                                          1170 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 4-methylisoxazolyl-3                                          1171 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 5-methylisothiazolyl-3                                        1172 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 4-methylisothiazolyl-3                                        1173 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 4-methyl-1,2,3-thiadiazolyl-5                                 1174 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 5-methyl-1,2,3-thiadiazolyl-4                                 1175 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl pyrryl-1                                                      1176 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl imidazolyl-1                                                  1177 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl pyrazolyl-1                                                   1178 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 1,3,4-triazolyl-1                                             1179 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 1,2,4-triazolyl-1                                             1180 H  H  CH.sub.3                                                                          NO.sub.2                                                                          2,5-dimethylthenyl-4                                          1181 H  H  CH.sub.3                                                                          NO.sub.2                                                                          5-methylthenyl-2                                              1182 H  H  CH.sub.3                                                                          NO.sub.2                                                                          pyrryl-2                                                      1183 H  H  CH.sub.3                                                                          NO.sub.2                                                                          pyrryl-3                                                      1184 H  H  CH.sub.3                                                                          NO.sub.2                                                                          oxazolyl-2                                                    1185 H  H  CH.sub.3                                                                          NO.sub.2                                                                          oxazolyl-4                                                    1186 H  H  CH.sub.3                                                                          NO.sub.2                                                                          oxazolyl-5                                                    1187 H  H  CH.sub.3                                                                          NO.sub.2                                                                          1,2,3-thiadiazolyl-4                                          1188 H  H  CH.sub.3                                                                          NO.sub.2                                                                          4-methyloxazolyl-5                                            1189 H  H  CH.sub. 3                                                                         NO.sub.2                                                                          thiazolyl-2                                                   1190 H  H  CH.sub.3                                                                          NO.sub.2                                                                          thiazolyl-4                                                   1191 H  H  CH.sub.3                                                                          NO.sub.2                                                                          thiazolyl-5                                                   1192 H  H  CH.sub.3                                                                          NO.sub.2                                                                          4-methylthiazolyl-5                                           1193 H  H  CH.sub.3                                                                          NO.sub.2                                                                          imidazolyl-4                                                  1194 H  H  CH.sub.3                                                                          NO.sub.2                                                                          imidazolyl-5                                                  1195 H  H  CH.sub.3                                                                          NO.sub.2                                                                          4-methylimidazolyl-5                                          1196 H  H  CH.sub.3                                                                          NO.sub.2                                                                          1-methylimidazolyl-5                                          1197 H  H  CH.sub.3                                                                          NO.sub.2                                                                          4-nitroimidazolyl-1                                           1198 H  H  CH.sub.3                                                                          NO.sub.2                                                                          2-methyl-4-nitroimidazolyl-1                                  1199 H  H  CH.sub.3                                                                          NO.sub.2                                                                          4,5-dichloroimidazolyl-1                                      1200 H  H  CH.sub.3                                                                          NO.sub.2                                                                          1-methylpyrryl-2                                              1201 H  H  CH.sub.3                                                                          NO.sub.2                                                                          isoxazolyl-3                                                  1202 H  H  CH.sub.3                                                                          NO.sub.2                                                                          isoxazolyl-4                                                  1203 H  H  CH.sub.3                                                                          NO.sub.2                                                                          isoxazolyl-5                                                  1204 H  H  CH.sub.3                                                                          NO.sub.2                                                                          5-chloromethylisoxazolyl-3                                    1205 H  H  CH.sub.3                                                                          NO.sub.2                                                                          isothiazolyl-3                                                1206 H  H  CH.sub.3                                                                          NO.sub.2                                                                          isothiazolyl-4                                                1207 H  H  CH.sub.3                                                                          NO.sub.2                                                                          isothiazolyl-5                                                1208 H  H  CH.sub.3                                                                          NO.sub.2                                                                          4-methylisothiazolyl-5                                        1209 H  H  CH.sub.3                                                                          NO.sub.2                                                                          pyrazolyl-4                                                   1210 H  H  CH.sub.3                                                                          NO.sub.2                                                                          pyrazolyl-5                                                   1211 H  H  CH.sub.3                                                                          NO.sub.2                                                                          1-methylpyrazolyl-5                                           1212 H  H  CH.sub.3                                                                          NO.sub.2                                                                          1,2,3-thiadiazolyl-5                                          1213 H  H  CH.sub.3                                                                          NO.sub.2                                                                          1,2,3-oxadiazolyl-5                                           1214 H  H  CH.sub. 3                                                                         NO.sub.2                                                                          1,2,3-oxadiazolyl-4                                           1215 H  H  CH.sub.3                                                                          NO.sub.2                                                                          5-methyl-1,2,3-oxadiazolyl-4                                  1216 H  H  CH.sub.3                                                                          NO.sub.2                                                                          4-methyl-1,2,3-oxadiazolyl-5                                  1217 H  H  CH.sub.3                                                                          NO.sub.2                                                                          1,3,4-thiadiazolyl-2                                          1218 H  H  CH.sub.3                                                                          NO.sub.2                                                                          2-methyl-1,3,4-thiadiazolyl-5                                 1219 H  H  CH.sub.3                                                                          NO.sub.2                                                                          1,2,4-thiadiazolyl-3                                          1220 H  H  CH.sub.3                                                                          NO.sub.2                                                                          1,2,4-thiadiazolyl-5                                          1221 H  H  CH.sub.3                                                                          NO.sub.2                                                                          3-methyl-1,2,4-thiadiazolyl-5                                 1222 H  H  CH.sub.3                                                                          NO.sub.2                                                                          1,2,4-oxadiazolyl-3                                           1223 H  H  CH.sub.3                                                                          NO.sub.2                                                                          1,2,4-oxadiazolyl-5                                           1224 H  H  CH.sub.3                                                                          NO.sub.2                                                                          1,2,4-triazolyl-5                                             1225 H  H  CH.sub.3                                                                          NO.sub.2                                                                          1,2,4-triazolyl-3                                             1226 H  H  CH.sub.3                                                                          NO.sub.2                                                                          1,3,4-oxadiazolyl-5                                           1227 H  H  CH.sub.3                                                                          NO.sub.2                                                                          2-methyl-1,3,4-oxadiazolyl-5                                  1228 H  H  CH.sub.3                                                                          NO.sub.2                                                                          1,2,5-oxadiazolyl-3                                           1229 H  H  CH.sub.3                                                                          NO.sub.2                                                                          3-methyl-1,2,5-oxadiazolyl-4                                  1230 H  H  CH.sub.3                                                                          NO.sub.2                                                                          1,2,5-thiadiazolyl-3                                          1231 H  H  CH.sub.3                                                                          NO.sub.2                                                                          3-methyl-1,2,5-thiadiazolyl-4                                 1232 H  H  CH.sub.3                                                                          NO.sub.2                                                                          2-methylfuryl-5                                               1233 H  H  CH.sub.3                                                                          NO.sub.2                                                                          2,5-dimethylfuryl-4                                           1235 H  H  CH.sub.3                                                                          NO.sub.2                                                                          5-methyloxazolyl-4                                            1234 H  H  CH.sub.3                                                                          NO.sub.2                                                                          4-methyloxazolyl-2                                            1236 H  H  CH.sub.3                                                                          NO.sub.2                                                                          5-methylisoxazolyl-3                                          1237 H  H  CH.sub.3                                                                          NO.sub.2                                                                          4-methylisoxazolyl-3                                          1238 H  H  CH.sub.3                                                                          NO.sub.2                                                                          5-methylisothiazolyl-3                                        1239 H  H  CH.sub. 3                                                                         NO.sub.2                                                                          4-methylisothiazolyl-3                                        1240 H  H  CH.sub.3                                                                          NO.sub.2                                                                          4-methyl-1,2,3-thiadiazolyl-5                                 1241 H  H  CH.sub.3                                                                          NO.sub.2                                                                          5-methyl-1,2,3-thiadiazolyl-4                                 1242 H  H  CH.sub.3                                                                          NO.sub.2                                                                          pyrryl-1                                                      1243 H  H  CH.sub.3                                                                          NO.sub.2                                                                          imidazolyl-1                                                  1244 H  H  CH.sub.3                                                                          NO.sub.2                                                                          pyrazolyl-1                                                   1245 H  H  CH.sub.3                                                                          NO.sub.2                                                                          1,3,4-triazolyl-1                                             1246 H  H  CH.sub.3                                                                          NO.sub.2                                                                          1,2,4-triazolyl-1                                             1247 H  H  H  I  thenyl-2                                                      1248 H  H  H  I  thenyl-3                                                      1249 H  H  H  I  2,5-dimethylthenyl-4                                          1250 H  H  H  I  5-methylthenyl-2                                              1251 H  H  H  I  pyrryl-2                                                      1252 H  H  H  I  pyrryl-3                                                      1253 H  H  H  I  oxazolyl-2                                                    1254 H  H  H  I  oxazolyl-4                                                    1255 H  H  H  I  oxazolyl-5                                                    1256 H  H  H  I  1,2,3-thiadiazolyl-4                                                                          177-178                                        1257 H  H  H  I  4-methyloxazolyl-5                                            1258 H  H  H  I  thiazolyl-2                                                   1259 H  H  H  I  thiazolyl-4                                                   1260 H  H  H  I  thiazolyl-5                                                   1261 H  H  H  I  4-methylthiazolyl-5                                           1262 H  H  H  I  imidazolyl-4                                                  1263 H  H  H  I  imidazolyl-5                                                  1264 H  H  H  I  4-methylimidazolyl-5                                          1265 H  H  H  I  1-methylimidazolyl-5                                          1266 H  H  H  I  4-nitroimidazolyl-1                                           1267 H  H  H  I  2-methyl-4-nitroimidazolyl-1                                  1268 H  H  H  I  4,5-dichloroimidazolyl-1                                      1269 H  H  H  I  1-methylpyrryl-2                                              1270 H  H  H  I  isoxazolyl-3   115-117                                        1271 H  H  H  I  isoxazolyl-4                                                  1272 H  H  H  I  isoxazolyl-5                                                  1273 H  H  H  I  5-chloromethylisoxazolyl-3                                    1274 H  H  H  I  isothiazolyl-3                                                1275 H  H  H  I  isothiazolyl-4                                                1276 H  H  H  I  isothiazolyl-5                                                1277 H  H  H  I  4-methylisothiazolyl-5                                        1278 H  H  H  I  pyrazolyl-4                                                   1279 H  H  H  I  pyrazolyl-5                                                   1280 H  H  H  I  1-methylpyrazolyl-5                                           1281 H  H  H  I  1,2,3-thiadiazolyl-5                                          1282 H  H  H  I  1,2,3-oxadiazolyl-5                                           1283 H  H  H  I  1,2,3-oxadiazolyl-4                                           1284 H  H  H  I  5-methyl-1,2,3-oxadiazolyl-4                                  1285 H  H  H  I  4-methyl-1,2,3-oxadiazolyl-5                                  1286 H  H  H  I  1,3,4-thiadiazolyl-2                                          1287 H  H  H  I  2-methyl-1,3,4-thiadiazolyl-5                                 1288 H  H  H  I  1,2,4-thiadiazolyl-3                                          1289 H  H  H  I  1,2,4-thiadiazolyl-5                                          1290 H  H  H  I  3-methyl-1,2,4-thiadiazolyl-5                                 1291 H  H  H  I  1,2,4-oxadiazolyl-3                                           1292 H  H  H  I  1,2,4-oxadiazolyl-5                                           1293 H  H  H  I  1,2,4-triazolyl-5                                             1294 H  H  H  I  1,2,4-triazolyl-3                                             1295 H  H  H  I  1,3,4-oxadiazolyl-5                                           1296 H  H  H  I  2-methyl-1,3,4-oxadiazolyl-5                                  1297 H  H  H  I  1,2,5-oxadiazolyl-3                                           1298 H  H  H  I  3-methyl-1,2,5-oxadiazolyl-4                                  1299 H  H  H  I  1,2,5-thiadiazolyl-3                                          1300 H  H  H  I  3-methyl-1,2,5-thiadiazolyl-4                                 1301 H  H  H  I  2-methylfuryl-5                                               1302 H  H  H  I  2,5-dimethylfuryl-4                                           1303 H  H  H  I  2-chlorofuryl-5                                               1304 H  H  H  I  5-methyloxazolyl-4                                            1305 H  H  H  I  4-methyloxazolyl-2                                            1306 H  H  H  I  5-methylisoxazolyl-3                                          1307 H  H  H  I  4-methylisoxazolyl-3                                          1308 H  H  H  I  5-methylisothiazolyl-3                                        1309 H  H  H  I  4-methylisothiazolyl-3                                        1310 H  H  H  I  4-methyl-1,2,3-thiadiazolyl-5                                 1311 H  H  H  I  5-methyl-1,2,3-thiadiazolyl-4                                 1312 H  H  H  I  pyrryl-1                                                      1313 H  H  H  I  imidazolyl-1                                                  1314 H  H  H  I  pyrazolyl-1                                                   1315 H  H  H  I  1,3,4-triazolyl-1                                             1316 H  H  H  I  1,2,4-triazolyl-1                                             1317 H  H  H  F  thenyl-2                                                      1318 H  H  H  F  thenyl-3                                                      1319 H  H  H  F  2,5-dimethylthenyl-4                                          1320 H  H  H  F  5-methylthenyl-2                                              1321 H  H  H  F  pyrryl-2                                                      1322 H  H  H  F  pyrryl-3                                                      1323 H  H  H  F  oxazolyl-2                                                    1324 H  H  H  F  oxazolyl-4                                                    1325 H  H  H  F  oxazolyl-5                                                    1326 H  H  H  F  1,2,3-thiadiazolyl-4                                          1327 H  H  H  F  4-methyloxazolyl-5                                            1328 H  H  H  F  thiazolyl-2                                                   1329 H  H  H  F  thiazolyl-4                                                   1330 H  H  H  F  thiazolyl-5                                                   1331 H  H  H  F  4-methylthiazolyl-5                                           1332 H  H  H  F  imidazolyl-4                                                  1333 H  H  H  F  imidazolyl-5                                                  1334 H  H  H  F  4-methylimidazolyl-5                                          1335 H  H  H  F  1-methylimidazolyl-5                                          1336 H  H  H  F  4-nitroimidazolyl-1                                           1337 H  H  H  F  2-methyl-4-nitroimidazolyl-1                                  1338 H  H  H  F  4,5-dichloroimidazolyl-1                                      1339 H  H  H  F  1-methylpyrryl-2                                              1340 H  H  H  F  isoxazolyl-3                                                  1341 H  H  H  F  isoxazolyl-4                                                  1342 H  H  H  F  isoxazolyl-5                                                  1343 H  H  H  F  5-chloromethylisoxazolyl-3                                    1344 H  H  H  F  isothiazolyl-3                                                1345 H  H  H  F  isothiazolyl-4                                                1346 H  H  H  F  isothiazolyl-5                                                1347 H  H  H  F  4-methylisothiazolyl-5                                        1348 H  H  H  F  pyrazolyl-4                                                   1349 H  H  H  F  pyrazolyl-5                                                   1350 H  H  H  F  1-methylpyrazolyl-5                                           1351 H  H  H  F  1,2,3-thiadiazolyl-5                                          1352 H  H  H  F  1,2,3-oxadiazolyl-5                                           1353 H  H  H  F  1,2,3-oxadiazolyl-4                                           1354 H  H  H  F  5-methyl-1,2,3-oxadiazolyl-4                                  1355 H  H  H  F  4-methyl-1,2,3-oxadiazolyl-5                                  1356 H  H  H  F  1,3,4-thiadiazolyl-2                                          1357 H  H  H  F  2-methyl-1,3,4-thiadiazolyl-5                                 1358 H  H  H  F  1,2,4-thiadiazolyl-3                                          1359 H  H  H  F  1,2,4-thiadiazolyl-5                                          1360 H  H  H  F  3-methyl-1,2,4-thiadiazolyl-5                                 1361 H  H  H  F  1,2,4-oxadiazolyl-3                                           1362 H  H  H  F  1,2,4-oxadiazolyl-5                                           1363 H  H  H  F  1,2,4-triazolyl-5                                             1364 H  H  H  F  1,2,4-triazolyl-3                                             1365 H  H  H  F  1,3,4-oxadiazolyl-5                                           1366 H  H  H  F  2-methyl-1,3,4-oxadiazolyl-5                                  1367 H  H  H  F  1,2,5-oxadiazolyl-3                                           1368 H  H  H  F  3-methyl-1,2,5-oxadiazolyl-4                                  1369 H  H  H  F  1,2,5-thiadiazolyl-3                                          1370 H  H  H  F  3-methyl-1,2,5-thiadiazolyl-4                                 1371 H  H  H  F  2-methylfuryl-5                                               1372 H  H  H  F  2,5-dimethylfuryl-4                                           1373 H  H  H  F  2-chlorofuryl-5                                               1374 H  H  H  F  5-methyloxazolyl-4                                            1375 H  H  H  F  4-methyloxazolyl-2                                            1376 H  H  H  F  5-methylisoxazolyl-3                                          1377 H  H  H  F  4-methylisoxazolyl-3                                          1378 H  H  H  F  5-methylisothiazolyl-3                                        1379 H  H  H  F  4-methylisothiazolyl-3                                        1380 H  H  H  F  4-methyl-1,2,3-thiadiazolyl-5                                 1381 H  H  H  F  5-methyl-1,2,3-thiadiazolyl-4                                 1382 H  H  H  F  pyrryl-1                                                      1383 H  H  H  F  imidazolyl-1                                                  1384 H  H  H  F  pyrazolyl-1                                                   1385 H  H  H  F  1,3,4-triazolyl-1                                             1386 H  H  H  F  1,2,4-triazolyl-1                                             1387 H  H  NO.sub.2                                                                          F  thenyl-2                                                      1388 H  H  NO.sub.2                                                                          F  thenyl-3                                                      1389 H  H  NO.sub.2                                                                          F  2,5-dimethylthenyl-4                                          1390 H  H  NO.sub.2                                                                          F  5-methylthenyl-2                                              1391 H  H  NO.sub.2                                                                          F  pyrryl-2                                                      1392 H  H  NO.sub.2                                                                          F  pyrryl-3                                                      1393 H  H  NO.sub.2                                                                          F  oxazolyl-2                                                    1394 H  H  NO.sub.2                                                                          F  oxazolyl-4                                                    1395 H  H  NO.sub.2                                                                          F  oxazolyl-5                                                    1396 H  H  NO.sub.2                                                                          F  1,2,3-thiadiazolyl-4                                          1397 H  H  NO.sub.2                                                                          F  4-methyloxazolyl-5                                            1398 H  H  NO.sub.2                                                                          F  thiazolyl-2                                                   1399 H  H  NO.sub.2                                                                          F  thiazolyl-4                                                   1400 H  H  NO.sub.2                                                                          F  thiazolyl-5                                                   1401 H  H  NO.sub.2                                                                          F  4-methylthiazolyl-5                                           1402 H  H  NO.sub.2                                                                          F  imidazolyl-4                                                  1403 H  H  NO.sub.2                                                                          F  imidazolyl-5                                                  1404 H  H  NO.sub.2                                                                          F  4-methylimidazolyl-5                                          1405 H  H  NO.sub.2                                                                          F  1-methylimidazolyl-5                                          1406 H  H  NO.sub.2                                                                          F  4-nitroimidazolyl-5                                           1407 H  H  NO.sub.2                                                                          F  2-methyl-4-nitroimidazolyl-1                                  1408 H  H  NO.sub.2                                                                          F  4,5-dichloroimidazolyl-1                                      1409 H  H  NO.sub.2                                                                          F  1-methylpyrryl-2                                              1410 H  H  NO.sub.2                                                                          F  isoxazolyl-3                                                  1411 H  H  NO.sub.2                                                                          F  isoxazolyl-4                                                  1412 H  H  NO.sub.2                                                                          F  isoxazolyl-5                                                  1413 H  H  NO.sub.2                                                                          F  5-chloromethylisoxazolyl-3                                    1414 H  H  NO.sub.2                                                                          F  isothiazolyl-3                                                1415 H  H  NO.sub.2                                                                          F  isothiazolyl-4                                                1416 H  H  NO.sub.2                                                                          F  isothiazolyl-5                                                1417 H  H  NO.sub.2                                                                          F  4-methylisothiazolyl-5                                        1418 H  H  NO.sub.2                                                                          F  pyrazolyl-4                                                   1419 H  H  NO.sub.2                                                                          F  pyrazolyl-5                                                   1420 H  H  NO.sub.2                                                                          F  1-methylpyrazolyl-5                                           1421 H  H  NO.sub.2                                                                          F  1,2,3-thiadiazolyl-5                                          1422 H  H  NO.sub.2                                                                          F  1,2,3-oxadiazolyl-5                                           1423 H  H  NO.sub.2                                                                          F  1,2,3-oxadiazolyl-4                                           1424 H  H  NO.sub.2                                                                          F  5-methyl-1,2,3-oxadiazolyl-4                                  1425 H  H  NO.sub.2                                                                          F  4-methyl-1,2,3-oxadiazolyl-5                                  1426 H  H  NO.sub.2                                                                          F  1,3,4-thiadiazolyl-2                                          1427 H  H  NO.sub.2                                                                          F  2-methyl-1,3,4-thiadiazolyl-5                                 1428 H  H  NO.sub.2                                                                          F  1,2,4-thiadiazolyl-3                                          1429 H  H  NO.sub.2                                                                          F  1,2,4-thiadiazolyl-5                                          1430 H  H  NO.sub.2                                                                          F  3-methyl-1,2,4-thiadiazolyl-5                                 1431 H  H  NO.sub.2                                                                          F  1,2,4-oxadiazolyl-3                                           1432 H  H  NO.sub.2                                                                          F  1,2,4-oxadiazolyl-5                                           1433 H  H  NO.sub.2                                                                          F  1,2,4-triazolyl-5                                             1434 H  H  NO.sub.2                                                                          F  1,2,4-triazolyl-3                                             1435 H  H  NO.sub.2                                                                          F  1,3,4-oxadiazolyl-5                                           1436 H  H  NO.sub.2                                                                          F  2-methyl-1,3,4-oxadiazolyl-5                                  1437 H  H  NO.sub.2                                                                          F  1,2,5-oxadiazolyl-3                                           1438 H  H  NO.sub.2                                                                          F  3-methyl-1,2,5-oxadiazolyl-4                                  1439 H  H  NO.sub.2                                                                          F  1,2,5-thiadiazolyl-3                                          1440 H  H  NO.sub.2                                                                          F  3-methyl-1,2,5-thiadiazolyl-4                                 1441 H  H  NO.sub.2                                                                          F  2-methylfuryl-5                                               1442 H  H  NO.sub.2                                                                          F  2,5-dimethylfuryl-4                                           1443 H  H  NO.sub.2                                                                          F  2-chlorofuryl-5                                               1444 H  H  NO.sub.2                                                                          F  5-methyloxazolyl-4                                            1445 H  H  NO.sub.2                                                                          F  4-methyloxazolyl-2                                            1446 H  H  NO.sub.2                                                                          F  5-methylisoxazolyl-3                                          1447 H  H  NO.sub.2                                                                          F  4-methylisoxazolyl-3                                          1448 H  H  NO.sub.2                                                                          F  5-methylisothiazolyl-3                                        1449 H  H  NO.sub.2                                                                          F  4-methylisothiazolyl-3                                        1450 H  H  NO.sub.2                                                                          F  4-methyl-1,2,3-thiadiazolyl-5                                 1451 H  H  NO.sub.2                                                                          F  5-methyl-1,2,3-thiadiazolyl-4                                 1452 H  H  NO.sub.2                                                                          F  pyrryl-1                                                      1453 H  H  NO.sub.2                                                                          F  imidazolyl-1                                                  1454 H  H  NO.sub.2                                                                          F  pyrazolyl-1                                                   1455 H  H  NO.sub.2                                                                          F  1,3,4-triazolyl-1                                             1456 H  H  NO.sub.2                                                                          F  1,2,4-triazolyl-1                                             1457 H  H  CH.sub.3                                                                          Cl 2,5-dimethylthenyl-4                                          1458 H  H  CH.sub.3                                                                          Cl 5-methylthenyl-2                                              1459 H  H  CH.sub.3                                                                          Cl pyrryl-2                                                      1460 H  H  CH.sub.3                                                                          Cl pyrryl-3                                                      1461 H  H  CH.sub.3                                                                          Cl oxazolyl-2                                                    1462 H  H  CH.sub.3                                                                          Cl oxazolyl-4                                                    1463 H  H  CH.sub.3                                                                          Cl oxazolyl-5                                                    1464 H  H  CH.sub.3                                                                          Cl 1,2,3-thiadiazolyl-4                                          1465 H  H  CH.sub.3                                                                          Cl 4-methyloxazolyl-5                                            1466 H  H  CH.sub.3                                                                          Cl thiazolyl-2                                                   1467 H  H  CH.sub.3                                                                          Cl thiazolyl-4                                                   1468 H  H  CH.sub.3                                                                          Cl thiazolyl-5                                                   1469 H  H  CH.sub.3                                                                          Cl 4-methylthiazolyl-5                                           1470 H  H  CH.sub.3                                                                          Cl imidazolyl-4                                                  1471 H  H  CH.sub.3                                                                          Cl imidazolyl-5                                                  1472 H  H  CH.sub.3                                                                          Cl 4-methylimidazolyl-5                                          1473 H  H  CH.sub.3                                                                          Cl 1-methylimidazolyl-5                                          1474 H  H  CH.sub.3                                                                          Cl 4-nitroimidazolyl-1                                           1475 H  H  CH.sub.3                                                                          Cl 2-methyl-4-nitroimidazolyl-1                                  1476 H  H  CH.sub.3                                                                          Cl 4,5-dichloroimidazolyl-1                                      1477 H  H  CH.sub.3                                                                          Cl 1-methylpyrryl-2                                              1478 H  H  CH.sub.3                                                                          Cl isoxazolyl-3                                                  1479 H  H  CH.sub.3                                                                          Cl isoxazolyl-4                                                  1480 H  H  CH.sub.3                                                                          Cl isoxazolyl-5                                                  1481 H  H  CH.sub.3                                                                          Cl 5-chloromethylisoxazolyl-3                                    1482 H  H  CH.sub.3                                                                          Cl isothiazolyl-3                                                1483 H  H  CH.sub.3                                                                          Cl isothiazolyl-4                                                1484 H  H  CH.sub.3                                                                          Cl isothiazolyl-5                                                1485 H  H  CH.sub.3                                                                          Cl 4-methylisothiazolyl-5                                        1486 H  H  CH.sub.3                                                                          Cl pyrazolyl-4                                                   1487 H  H  CH.sub.3                                                                          Cl pyrazolyl-5                                                   1488 H  H  CH.sub.3                                                                          Cl 1-methylpyrazolyl-5                                           1489 H  H  CH.sub.3                                                                          Cl 1,2,3-thiadiazolyl-5                                          1490 H  H  CH.sub.3                                                                          Cl 1,2,3-oxadiazolyl-5                                           1491 H  H  CH.sub.3                                                                          Cl 1,2,3-oxadiazolyl-4                                           1492 H  H  CH.sub.3                                                                          Cl 5-methyl-1,2,3-oxadiazolyl-4                                  1493 H  H  CH.sub.3                                                                          Cl 4-methyl-1,2,3-oxadiazolyl-5                                  1494 H  H  CH.sub.3                                                                          Cl 1,3,4-thiadiazolyl-2                                          1495 H  H  CH.sub.3                                                                          Cl 2-methyl-1,3,4-thiadiazolyl-5                                 1496 H  H  CH.sub.3                                                                          Cl 1,2,4-thiadiazolyl-3                                          1497 H  H  CH.sub.3                                                                          Cl 1,2,4-thiadiazolyl-5                                          1498 H  H  CH.sub.3                                                                          Cl 3-methyl-1,2,4-thiadiazolyl-5                                 1499 H  H  CH.sub.3                                                                          Cl 1,2,4-oxadiazolyl-3                                           1500 H  H  CH.sub.3                                                                          Cl 1,2,4-oxadiazolyl-5                                           1501 H  H  CH.sub.3                                                                          Cl 1,2,4-triazolyl-5                                             1502 H  H  CH.sub.3                                                                          Cl 1,2,4-triazolyl-3                                             1503 H  H  CH.sub.3                                                                          Cl 1,3,4-oxadiazolyl-5                                           1504 H  H  CH.sub.3                                                                          Cl 2-methyl-1,3,4-oxadiazolyl-5                                  1505 H  H  CH.sub.3                                                                          Cl 1,2,5-oxadiazolyl-3                                           1506 H  H  CH.sub.3                                                                          Cl 3-methyl-1,2,5-oxadiazolyl-4                                  1507 H  H  CH.sub.3                                                                          Cl 1,2,5-thiadiazolyl-3                                          1508 H  H  CH.sub.3                                                                          Cl 3-methyl-1,2,5-thiadiazolyl-4                                 1509 H  H  CH.sub.3                                                                          Cl 2-methylfuryl-5                                               1510 H  H  CH.sub.3                                                                          Cl 2,5-dimethylfuryl-4                                           1511 H  H  CH.sub.3                                                                          Cl 2-chlorofuryl-5                                               1512 H  H  CH.sub.3                                                                          Cl 5-methyloxazolyl-4                                            1513 H  H  CH.sub.3                                                                          Cl 4-methyloxazolyl-2                                            1514 H  H  CH.sub.3                                                                          Cl 5-methylisoxazolyl-3                                          1515 H  H  CH.sub.3                                                                          Cl 4-methylisoxazolyl-2                                          1516 H  H  CH.sub.3                                                                          Cl 5-methylisothiazolyl-3                                        1517 H  H  CH.sub.3                                                                          Cl 4-methylisothiazolyl-3                                        1518 H  H  CH.sub.3                                                                          Cl 4-methyl-1,2,3-thiadiazolyl-5                                 1519 H  H  CH.sub.3                                                                          Cl 5-methyl-1,2,3-thiadiazolyl-4                                 1520 H  H  CH.sub.3                                                                          Cl pyrryl-1                                                      1521 H  H  CH.sub.3                                                                          Cl imidazolyl-1                                                  1522 H  H  CH.sub.3                                                                          Cl pyrazolyl-1                                                   1523 H  H  CH.sub.3                                                                          Cl 1,3,4-triazolyl-1                                             1524 H  H  CH.sub.3                                                                          Cl 1,2,4-triazolyl-1                                             1525 H  H  I  H  thenyl-2                                                      1526 H  H  I  H  thenyl-3                                                      1527 H  H  I  H  2,5-dimethylthenyl-4                                          1528 H  H  I  H  5-methylthenyl-2                                              1529 H  H  I  H  pyrryl-2                                                      1530 H  H  I  H  pyrryl-3                                                      1531 H  H  I  H  oxazolyl-2                                                    1532 H  H  I  H  oxazolyl-4                                                    1533 H  H  I  H  oxazolyl-5                                                    1534 H  H  I  H  1,2,3-thiadiazolyl-4                                          1535 H  H  I  H  4-methyloxazolyl-5                                            1536 H  H  I  H  thiazolyl-2                                                   1537 H  H  I  H  thiazolyl-4                                                   1538 H  H  I  H  thiazolyl-5                                                   1539 H  H  I  H  4-methylthiazolyl-5                                           1540 H  H  I  H  imidazolyl-4                                                  1541 H  H  I  H  imidazolyl-5                                                  1542 H  H  I  H  4-methylimidazolyl-5                                          1543 H  H  I  H  1-methylimidazolyl-5                                          1544 H  H  I  H  4-nitroimidazolyl-1                                           1545 H  H  I  H  2-methyl-4-nitroimidazolyl-1                                  1546 H  H  I  H  4,5-dichloroimidazolyl-1                                      1547 H  H  I  H  1-methylpyrryl-2                                              1548 H  H  I  H  isoxazolyl-3                                                  1549 H  H  I  H  isoxazolyl-4                                                  1550 H  H  I  H  isoxazolyl-5                                                  1551 H  H  I  H  5-chloromethylisoxazolyl-3                                    1552 H  H  I  H  isothiazolyl-3                                                1553 H  H  I  H  isothiazolyl-4                                                1554 H  H  I  H  isothiazolyl-5                                                1555 H  H  I  H  4-methylisothiazolyl-5                                        1556 H  H  I  H  pyrazolyl-4                                                   1557 H  H  I  H  pyrazolyl-5                                                   1558 H  H  I  H  1-methylpyrazolyl-5                                           1559 H  H  I  H  1,2,3-thiadiazolyl-5                                          1560 H  H  I  H  1,2,3-oxadiazolyl-5                                           1561 H  H  I  H  1,2,3-oxadiazolyl-4                                           1562 H  H  I  H  5-methyl-1,2,3-oxadiazolyl-4                                  1563 H  H  I  H  4-methyl-1,2,3-oxadiazolyl-5                                  1564 H  H  I  H  1,3,4-thiadiazolyl-2                                          1565 H  H  I  H  2-methyl-1,3,4-thiadiazolyl-5                                 1566 H  H  I  H  1,2,4-thiadiazolyl-3                                          1567 H  H  I  H  1,2,4-thiadiazolyl-5                                          1568 H  H  I  H  3-methyl-1,2,4-thiadiazolyl-5                                 1569 H  H  I  H  1,2,4-oxadiazolyl-3                                           1570 H  H  I  H  1,2,4-oxadiazolyl-5                                           1571 H  H  I  H  1,2,4-triazolyl-5                                             1572 H  H  I  H  1,2,4-triazolyl-3                                             1573 H  H  I  H  1,3,4-oxadiazolyl-5                                           1574 H  H  I  H  2-methyl-1,3,4-oxadiazolyl-5                                  1575 H  H  I  H  1,2,5-oxadiazolyl-3                                           1576 H  H  I  H  3-methyl-1,2,5-oxadiazolyl-4                                  1577 H  H  I  H  1,2,5-thiadiazolyl-3                                          1578 H  H  I  H  3-methyl-1,2,5-thiadiazolyl-4                                 1579 H  H  I  H  2-methylfuryl-5                                               1580 H  H  I  H  2,5-dimethylfuryl-4                                           1581 H  H  I  H  2-chlorofuryl-5                                               1582 H  H  I  H  5-methyloxazolyl-4                                            1583 H  H  I  H  4-methyloxazolyl-2                                            1584 H  H  I  H  5-methylisoxazolyl-3                                          1585 H  H  I  H  4-methylisoxazolyl-3                                          1586 H  H  I  H  5-methylisothiazolyl-3                                        1587 H  H  I  H  4-methylisothiazolyl-3                                        1588 H  H  I  H  4-methyl-1,2,3-thiadiazolyl-5                                 1589 H  H  I  H  5-methyl-1,2,3-thiadiazolyl-4                                 1590 H  H  I  H  pyrryl-1                                                      1591 H  H  I  H  imidazolyl-1                                                  1592 H  H  I  H  pyrazolyl-1                                                   1593 H  H  I  H  1,3,4-triazolyl-1                                             1594 H  H  I  H  1,2,4-triazolyl-1                                             1595 H  H  I  NO.sub.2                                                                          thenyl-2                                                      1596 H  H  I  NO.sub.2                                                                          thenyl-3                                                      1597 H  H  I  NO.sub.2                                                                          pyrryl-2                                                      1598 H  H  I  NO.sub.2                                                                          pyrryl-3                                                      1599 H  H  I  NO.sub.2                                                                          oxazolyl-2                                                    1600 H  H  I  NO.sub.2                                                                          oxazolyl-4                                                    1601 H  H  I  NO.sub.2                                                                          1,2,3-thiadiazolyl-4                                          1602 H  H  I  NO.sub.2                                                                          thiazolyl-2                                                   1603 H  H  I  NO.sub.2                                                                          thiazolyl-4                                                   1604 H  H  I  NO.sub.2                                                                          thiazolyl-5                                                   1605 H  H  I  NO.sub.2                                                                          imidazolyl-4                                                  1606 H  H  I  NO.sub.2                                                                          imidazolyl-5                                                  1607 H  H  I  NO.sub.2                                                                          isoxazolyl-3                                                  1608 H  H  I  NO.sub.2                                                                          isoxazolyl-4                                                  1609 H  H  I  NO.sub.2                                                                          isoxazolyl-5                                                  1610 H  H  I  NO.sub. 2                                                                         5-chloromethylisoxazolyl-3                                    1611 H  H  I  NO.sub.2                                                                          isothiazolyl-3                                                1612 H  H  I  NO.sub.2                                                                          isothiazolyl-4                                                1613 H  H  I  NO.sub.2                                                                          pyrazolyl-4                                                   1614 H  H  I  NO.sub.2                                                                          pyrazolyl-5                                                   1615 H  H  I  NO.sub.2                                                                          1,2,3-thiadiazolyl-5                                          1616 H  H  I  NO.sub.2                                                                          1,2,3-oxadiazolyl-5                                           1617 H  H  I  NO.sub.2                                                                          1,2,3-oxadiazolyl-4                                           1618 H  H  I  NO.sub.2                                                                          1,3,4-thiadiazolyl-2                                          1619 H  H  I  NO.sub.2                                                                          2-methyl-1,3,4-thiadiazolyl-5                                 1620 H  H  I  NO.sub.2                                                                          2-methyl-1,3,4-oxadiazolyl-5                                  1621 H  H  I  NO.sub.2                                                                          2-methylfuryl-5                                               1622 H  H  I  NO.sub.2                                                                          2,5-dimethylfuryl-4                                           1623 H  H  I  NO.sub.2                                                                          4-methyl-1,2,3-thiadiazolyl-5                                 1624 H  H  I  NO.sub.2                                                                          5-methyl-1,2,3-thiadiazolyl-4                                 1625 H  H  I  NO.sub.2                                                                          pyrryl-1                                                      1626 H  H  I  NO.sub.2                                                                          imidazolyl-1                                                  1627 H  H  I  NO.sub.2                                                                          pyrazolyl-1                                                   1628 H  H  I  NO.sub.2                                                                          1,3,4-triazolyl-1                                             1629 H  H  I  NO.sub.2                                                                          1,2,4-triazolyl-1                                             1630 H  H  I  NO.sub.2                                                                          isothiazolyl-5                                                1631 H  H  F  NO.sub.2                                                                          thenyl-2                                                      1632 H  H  F  NO.sub.2                                                                          thenyl-3                                                      1633 H  H  F  NO.sub.2                                                                          pyrryl-2                                                      1634 H  H  F  NO.sub.2                                                                          pyrryl-3                                                      1635 H  H  F  NO.sub.2                                                                          oxazolyl-2                                                    1636 H  H  F  NO.sub.2                                                                          oxazolyl-4                                                    1637 H  H  F  NO.sub.2                                                                          1,2,3-thiadiazolyl-4                                          1638 H  H  F  NO.sub.2                                                                          thiazolyl-2                                                   1639 H  H  F  NO.sub.2                                                                          thiazolyl-4                                                   1640 H  H  F  NO.sub.2                                                                          thiazolyl-5                                                   1641 H  H  F  NO.sub.2                                                                          imidazolyl-4                                                  1642 H  H  F  NO.sub.2                                                                          imidazolyl-5                                                  1643 H  H  F  NO.sub.2                                                                          isoxazolyl-3                                                  1644 H  H  F  NO.sub.2                                                                          isoxazolyl-4                                                  1645 H  H  F  NO.sub.2                                                                          isoxazolyl-5                                                  1646 H  H  F  NO.sub.2                                                                          5-chloromethylisoxazolyl-3                                    1647 H  H  F  NO.sub.2                                                                          isothiazolyl-3                                                1648 H  H  F  NO.sub.2                                                                          isothiazolyl-4                                                1649 H  H  F  NO.sub.2                                                                          pyrazolyl-4                                                   1650 H  H  F  NO.sub.2                                                                          pyrazolyl-5                                                   1651 H  H  F  NO.sub.2                                                                          1,2,3-thiadiazolyl-5                                          1652 H  H  F  NO.sub.2                                                                          1,2,3-oxadiazolyl-5                                           1653 H  H  F  NO.sub.2                                                                          1,2,3-oxadiazolyl-4                                           1654 H  H  F  NO.sub.2                                                                          1,3,4-thiadiazolyl-2                                          1655 H  H  F  NO.sub.2                                                                          2-methyl-1,3,4-thiadiazolyl-5                                 1656 H  H  F  NO.sub.2                                                                          2-methyl-1,3,4-oxadiazolyl-5                                  1657 H  H  F  NO.sub.2                                                                          2-methylfuryl-5                                               1658 H  H  F  NO.sub.2                                                                          2,5-dimethylfuryl-4                                           1659 H  H  F  NO.sub.2                                                                          4-methyl-1,2,3-thiadiazolyl-5                                 1660 H  H  F  NO.sub.2                                                                          5-methyl-1,2,3-thiadiazolyl-4                                 1661 H  H  F  NO.sub.2                                                                          pyrryl-1                                                      1662 H  H  F  NO.sub.2                                                                          imidazolyl-1                                                  1663 H  H  F  NO.sub.2                                                                          pyrazolyl-1                                                   1664 H  H  F  NO.sub.2                                                                          1,3,4-triazolyl-1                                             1665 H  H  F  NO.sub.2                                                                          1,2,4-triazolyl-1                                             1666 H  H  F  NO.sub.2                                                                          isothiazolyl-5                                                1667 H  H  CH.sub.3                                                                          H  pyrryl-2                                                      1668 H  H  CH.sub.3                                                                          H  pyrryl-3                                                      1669 H  H  CH.sub.3                                                                          H  oxazolyl-2                                                    1670 H  H  CH.sub.3                                                                          H  oxazolyl-4                                                    1671 H  H  CH.sub.3                                                                          H  1,2,3-thiadiazolyl-4                                          1672 H  H  CH.sub.3                                                                          H  thiazolyl-2                                                   1673 H  H  CH.sub.3                                                                          H  thiazolyl-4                                                   1674 H  H  CH.sub.3                                                                          H  thiazolyl-5                                                   1675 H  H  CH.sub.3                                                                          H  imidazolyl-4                                                  1676 H  H  CH.sub.3                                                                          H  imidazolyl-5                                                  1677 H  H  CH.sub.3                                                                          H  isoxazolyl-3   146-148                                        1678 H  H  CH.sub.3                                                                          H  isoxazolyl-4                                                  1679 H  H  CH.sub.3                                                                          H  isoxazolyl-5   129-132                                        1680 H  H  CH.sub.3                                                                          H  5-chloromethylisoxazolyl-3                                    1681 H  H  CH.sub.3                                                                          H  isothiazolyl-3                                                1682 H  H  CH.sub.3                                                                          H  isothiazolyl-4                                                1683 H  H  CH.sub.3                                                                          H  pyrazolyl-4                                                   1684 H  H  CH.sub.3                                                                          H  pyrazolyl-5                                                   1685 H  H  CH.sub.3                                                                          H  1,2,3-thiadiazolyl-5                                          1686 H  H  CH.sub.3                                                                          H  1,2,3-oxadiazolyl-5                                           1687 H  H  CH.sub.3                                                                          H  1,2,3-oxadiazolyl-4                                           1688 H  H  CH.sub.3                                                                          H  1,3,4-thiadiazolyl-2                                          1689 H  H  CH.sub.3                                                                          H  2-methyl-1,3,4-thiadiazolyl-5                                 1690 H  H  CH.sub.3                                                                          H  2-methyl-1,3,4-oxadiazolyl-5                                  1691 H  H  CH.sub.3                                                                          H  2-methylfuryl-5                                               1692 H  H  CH.sub.3                                                                          H  2,5-dimethylfuryl-4                                                                           160-164                                        1693 H  H  CH.sub.3                                                                          H  4-methyl-1,2,3-thiadiazolyl-5                                                                 162-166                                        1694 H  H  CH.sub.3                                                                          H  5-methyl-1,2,3-thiadiazolyl-4                                 1695 H  H  CH.sub.3                                                                          H  pyrryl-1                                                      1696 H  H  CH.sub.3                                                                          H  imidazolyl-1   156-158                                        1697 H  H  CH.sub.3                                                                          H  pyrazolyl-1                                                   1698 H  H  CH.sub.3                                                                          H  1,3,4-triazolyl-1                                             1699 H  H  CH.sub.3                                                                          H  1,2,4-triazolyl-1                                             1700 H  H  CH.sub.3                                                                          H  isothiazolyl-5                                                1701 CH.sub.3                                                                          H  H  Cl thenyl-2                                                      1702 CH.sub.3                                                                          H  H  Cl thenyl-3                                                      1703 CH.sub.3                                                                          H  H  Cl pyrryl-2                                                      1704 CH.sub.3                                                                          H  H  Cl pyrryl-3                                                      1705 CH.sub.3                                                                          H  H  Cl oxazolyl-2                                                    1706 CH.sub.3                                                                          H  H  Cl oxazolyl-4                                                    1707 CH.sub.3                                                                          H  H  Cl 1,2,3-thiadiazolyl-4                                                                          127-130                                        1708 CH.sub.3                                                                          H  H  Cl thiazolyl-2                                                   1709 CH.sub.3                                                                          H  H  Cl thiazolyl-4                                                   1710 CH.sub.3                                                                          H  H  Cl thiazolyl-5                                                   1711 CH.sub.3                                                                          H  H  Cl imidazolyl-4                                                  1712 CH.sub.3                                                                          H  H  Cl imidazolyl-5                                                  1713 CH.sub.3                                                                          H  H  Cl isoxazolyl-3   113-117                                        1714 CH.sub.3                                                                          H  H  Cl isoxazolyl-4                                                  1715 CH.sub.3                                                                          H  H  Cl isoxazolyl-5   106-110                                        1716 CH.sub.3                                                                          H  H  Cl 5-chloromethylisoxazolyl-3                                    1717 CH.sub.3                                                                          H  H  Cl isothiazolyl-3                                                1718 CH.sub.3                                                                          H  H  Cl isothiazolyl-4                                                1719 CH.sub.3                                                                          H  H  Cl pyrazolyl-4                                                   1720 CH.sub.3                                                                          H  H  Cl pyrazolyl-5                                                   1721 CH.sub.3                                                                          H  H  Cl 1,2,3-thiadiazolyl-5                                          1722 CH.sub.3                                                                          H  H  Cl 1,2,3-oxadiazolyl-5                                           1723 CH.sub.3                                                                          H  H  Cl 1,2,3-oxadiazolyl-4                                           1724 CH.sub.3                                                                          H  H  Cl 1,3,4-thiadiazolyl-2                                          1725 CH.sub.3                                                                          H  H  Cl 2-methyl-1,3,4-thiadiazolyl-5                                 1726 CH.sub.3                                                                          H  H  Cl 2-methyl-1,3,4-oxadiazolyl-5                                  1727 CH.sub.3                                                                          H  H  Cl 2-methylfuryl-5                                               1728 CH.sub.3                                                                          H  H  Cl 2,5-dimethylfuryl-4                                           1729 CH.sub.3                                                                          H  H  Cl 4-methyl-1,2,3-thiadiazolyl-5                                                                 140-142                                        1730 CH.sub.3                                                                          H  H  Cl 5-methyl-1,2,3-thiadiazolyl-4                                 1731 CH.sub.3                                                                          H  H  Cl pyrryl-1                                                      1732 CH.sub.3                                                                          H  H  Cl imidazolyl-1                                                  1733 CH.sub.3                                                                          H  H  Cl pyrazolyl-1                                                   1734 CH.sub.3                                                                          H  H  Cl 1,3,4-triazolyl-1                                             1735 CH.sub.3                                                                          H  H  Cl 1,2,4-triazolyl-1                                             1736 CH.sub.3                                                                          H  H  Cl isothiazolyl-5                                                1737 CH.sub.3                                                                          H  Cl H  thenyl-2                                                      1738 CH.sub.3                                                                          H  Cl H  thenyl-3                                                      1739 CH.sub.3                                                                          H  Cl H  pyrryl-2                                                      1740 CH.sub.3                                                                          H  Cl H  pyrryl-3                                                      1741 CH.sub.3                                                                          H  Cl H  oxazolyl-2                                                    1742 CH.sub.3                                                                          H  Cl H  oxazolyl-4                                                    1743 CH.sub.3                                                                          H  Cl H  1,2,3-thiadiazolyl-4                                                                          155-157                                        1744 CH.sub.3                                                                          H  Cl H  thiazolyl-2                                                   1745 CH.sub.3                                                                          H  Cl H  thiazolyl-4                                                   1746 CH.sub.3                                                                          H  Cl H  thiazolyl-5                                                   1747 CH.sub.3                                                                          H  Cl H  imidazolyl-4                                                  1748 CH.sub.3                                                                          H  Cl H  imidazolyl-5                                                  1749 CH.sub.3                                                                          H  Cl H  isoxazolyl-3   128-130                                        1750 CH.sub.3                                                                          H  Cl H  isoxazolyl-4                                                  1751 CH.sub.3                                                                          H  Cl H  isoxazolyl-5                                                  1752 CH.sub.3                                                                          H  Cl H  5-chloromethylisoxazolyl-3                                    1753 CH.sub.3                                                                          H  Cl H  isothiazolyl-3                                                1754 CH.sub.3                                                                          H  Cl H  isothiazolyl-4                                                1755 CH.sub.3                                                                          H  Cl H  pyrazolyl-4                                                   1756 CH.sub.3                                                                          H  Cl H  pyrazolyl-5                                                   1757 CH.sub.3                                                                          H  Cl H  1,2,3-thiadiazolyl-5                                          1758 CH.sub.3                                                                          H  Cl H  1,2,3-oxadiazolyl-5                                           1759 CH.sub.3                                                                          H  Cl H  1,2,3-oxadiazolyl-4                                           1760 CH.sub.3                                                                          H  Cl H  1,3,4-thiadiazolyl-2                                          1761 CH.sub.3                                                                          H  Cl H  2-methyl-1,3,4-thiadiazolyl-5                                 1762 CH.sub.3                                                                          H  Cl H  2-methyl-1,3,4-oxadiazolyl-5                                  1763 CH.sub.3                                                                          H  Cl H  2-methylfuryl-5                                               1764 CH.sub.3                                                                          H  Cl H  2,5-dimethylfuryl-4                                                                           100-102                                        1765 CH.sub.3                                                                          H  Cl H  4-methyl-1,2,3-thiadiazolyl-5                                                                 161-163                                        1766 CH.sub.3                                                                          H  Cl H  5-methyl-1,2,3-thiadiazolyl-4                                 1767 CH.sub.3                                                                          H  Cl H  pyrryl-1                                                      1768 CH.sub.3                                                                          H  Cl H  imidazolyl-1                                                  1769 CH.sub.3                                                                          H  Cl H  pyrazolyl-1                                                   1770 CH.sub.3                                                                          H  Cl H  1,3,4-triazolyl-1                                             1771 CH.sub.3                                                                          H  Cl H  1,2,4-triazolyl-1                                             1772 CH.sub.3                                                                          H  Cl H  isothiazolyl-5                                                1773 CH.sub.3                                                                          H  NO.sub.2                                                                          H  thenyl-2                                                      1774 CH.sub.3                                                                          H  NO.sub.2                                                                          H  thenyl-3                                                      1775 CH.sub.3                                                                          H  NO.sub.2                                                                          H  pyrryl-2                                                      1776 CH.sub.3                                                                          H  NO.sub.2                                                                          H  pyrryl-3                                                      1777 CH.sub.3                                                                          H  NO.sub.2                                                                          H  oxazolyl-2                                                    1778 CH.sub.3                                                                          H  NO.sub.2                                                                          H  oxazolyl-4                                                    1779 CH.sub.3                                                                          H  NO.sub.2                                                                          H  1,2,3-thiadiazolyl-4                                          1780 CH.sub.3                                                                          H  NO.sub.2                                                                          H  thiazolyl-2                                                   1781 CH.sub.3                                                                          H  NO.sub.2                                                                          H  thiazolyl-4                                                   1782 CH.sub.3                                                                          H  NO.sub.2                                                                          H  thiazolyl-5                                                   1783 CH.sub.3                                                                          H  NO.sub.2                                                                          H  imidazolyl-4                                                  1784 CH.sub.3                                                                          H  NO.sub.2                                                                          H  imidazolyl-5                                                  1785 CH.sub.3                                                                          H  NO.sub.2                                                                          H  isoxazolyl-3                                                  1786 CH.sub.3                                                                          H  NO.sub.2                                                                          H  isoxazolyl-4                                                  1787 CH.sub.3                                                                          H  NO.sub.2                                                                          H  isoxazolyl-5                                                  1788 CH.sub.3                                                                          H  NO.sub.2                                                                          H  5-chloromethylisoxazolyl-3                                    1789 CH.sub.3                                                                          H  NO.sub.2                                                                          H  isothiazolyl-3                                                1790 CH.sub.3                                                                          H  NO.sub.2                                                                          H  isothiazolyl-4                                                1791 CH.sub.3                                                                          H  NO.sub.2                                                                          H  pyrazolyl-4                                                   1792 CH.sub.3                                                                          H  NO.sub.2                                                                          H  pyrazolyl-5                                                   1793 CH.sub.3                                                                          H  NO.sub.2                                                                          H  1,2,3-thiadiazolyl-5                                          1794 CH.sub.3                                                                          H  NO.sub.2                                                                          H  1,2,3-oxadiazolyl-5                                           1795 CH.sub.3                                                                          H  NO.sub.2                                                                          H  1,2,3-oxadiazolyl-4                                           1796 CH.sub.3                                                                          H  NO.sub.2                                                                          H  1,3,4-thiadiazolyl-2                                          1797 CH.sub.3                                                                          H  NO.sub.2                                                                          H  2-methyl-1,3,4-thiadiazolyl-5                                 1798 CH.sub.3                                                                          H  NO.sub.2                                                                          H  2-methyl-1,3,4-oxadiazolyl-5                                  1799 CH.sub.3                                                                          H  NO.sub.2                                                                          H  2-methylfuryl-5                                               1800 CH.sub.3                                                                          H  NO.sub.2                                                                          H  2,5-dimethylfuryl-4                                           1801 CH.sub.3                                                                          H  NO.sub.2                                                                          H  4-methyl-1,2,3-thiadiazolyl-5                                 1802 CH.sub.3                                                                          H  NO.sub.2                                                                          H  5-methyl-1,2,3-thiadiazolyl-4                                 1803 CH.sub.3                                                                          H  NO.sub.2                                                                          H  pyrryl-1                                                      1804 CH.sub.3                                                                          H  NO.sub.2                                                                          H  imidazolyl-1                                                  1805 CH.sub.3                                                                          H  NO.sub.2                                                                          H  pyrazolyl-1                                                   1806 CH.sub.3                                                                          H  NO.sub.2                                                                          H  1,3,4-triazolyl-1                                             1807 CH.sub.3                                                                          H  NO.sub.2                                                                          H  1,2,4-triazolyl-1                                             1808 CH.sub.3                                                                          H  NO.sub.2                                                                          H  isothiazolyl-5                                                1809 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          thenyl-2                                                      1810 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          thenyl-3                                                      1811 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          pyrryl-2                                                      1812 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          pyrryl-3                                                      1813 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          oxazolyl-2                                                    1814 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          oxazolyl-4                                                    1815 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          1,2,3-thiadiazolyl-4                                          1816 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          thiazolyl-2                                                   1817 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          thiazolyl-4                                                   1818 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          thiazolyl-5                                                   1819 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          imidazolyl-4                                                  1820 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          imidazolyl-5                                                  1821 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          isoxazolyl-3                                                  1822 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          isoxazolyl-4                                                  1823 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          isoxazolyl-5                                                  1824 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          5-chloromethylisoxazolyl-3                                    1825 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          isothiazolyl-3                                                1826 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          isothiazolyl-4                                                1827 H  Cl NO.sub.2                                                                          NO.sub. 2                                                                         pyrazolyl-4                                                   1828 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          pyrazolyl-5                                                   1829 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          1,2,3-thiadiazolyl-5                                          1830 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          1,2,3-oxadiazolyl-5                                           1831 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          1,2,3-oxadiazolyl-4                                           1832 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          1,3,4-thiadiazolyl-2                                          1833 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          2-methyl-1,3,4-thiadiazolyl-5                                 1834 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          2-methyl-1,3,4-oxadiazolyl-5                                  1835 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          2-methylfuryl-5                                               1836 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          2,5-dimethylfuryl-4                                           1837 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          4-methyl-1,2,3-thiadiazolyl-5                                 1838 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          5-methyl-1,2,3-thiadiazolyl-4                                 1839 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          pyrryl-1                                                      1840 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          imidazolyl-1                                                  1841 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          pyrazolyl-1                                                   1842 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          1,3,4-triazolyl-1                                             1843 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          1,2,4-triazolyl-1                                             1844 H  Cl NO.sub.2                                                                          NO.sub.2                                                                          isothiazolyl-5                                                1845 H  H  CH.sub.3                                                                          Br 2,5-dimethylfuryl-4                                                                           120-122                                        1846 H  H  NO.sub.2                                                                          H  3,5-dimethylisoxazolyl-4                                                                      205-207                                        1847 H  H  H  Cl 3,5-dimethylisoxazolyl-4                                      1848 H  H  H  Br 3,5-dimethylisoxazolyl-4                                      1849 H  H  H  NO.sub.2                                                                          3,5-dimethylisoxazolyl-4                                      1850 H  H  NO.sub.2                                                                          Cl 3,5-dimethylisoxazolyl-4                                      1851 H  H  NO.sub.2                                                                          Br 3,5-dimethylisoxazolyl-4                                      1852 H  H  NO.sub.2                                                                          I  3,5-dimethylisoxazolyl-4                                      1853 H  H  Cl H  3,5-dimethylisoxazolyl-4                                      1854 H  H  Cl NO.sub.2                                                                          3,5-dimethylisoxazolyl-4                                      1855 H  H  Br NO.sub.2                                                                          3,5-dimethylisoxazolyl-4                                      1856 H  H  Br H  3,5-dimethylisoxazolyl-4                                      1857 H  H  NO.sub.2                                                                          NO.sub.2                                                                          3,5-dimethylisoxazolyl-4                                      1858 CH.sub.3                                                                          H  NO.sub.2                                                                          NO.sub.2                                                                          3,5-dimethylisoxazolyl-4                                      1859 CH.sub.3                                                                          H  NO.sub.2                                                                          Cl 3,5-dimethylisoxazolyl-4                                      1860 H  H  CH.sub.3                                                                          NO.sub.2                                                                          3,5-dimethylisoxazolyl-4                                      1861 H  H  CH.sub.3                                                                          Cl 3,5-dimethylisoxazolyl-4                                      1862 H  H  I  H  3,5-dimethylisoxazolyl-4                                      1863 H  H  I  NO.sub.2                                                                          3,5-dimethylisoxazolyl-4                                      1864 H  H  CH.sub.3                                                                          H  3,5-dimethylisoxazolyl-4                                      1865 CH.sub.3                                                                          H  H  Cl 3,5-dimethylisoxazolyl-4                                      1866 CH.sub.3                                                                          H  Cl H  3,5-dimethylisoxazolyl-4                                      1867 CH.sub.3                                                                          H  NO.sub.2                                                                          H  3,5-dimethylisoxazolyl-4                                      1868 H  H  CH.sub.3                                                                          Br isoxazolyl-3   138-141                                        1869 H  H  CH.sub.3                                                                          Br isoxazolyl-5                                                  1870 H  H  CH.sub.3                                                                          Br 4-methyl-1,2,3-thiadiazolyl-5                                 1871 H  H  CH.sub.3                                                                          Br 1,2,3-thiadiazolyl-4                                                                          175-177                                        1872 H  H  CH.sub.3                                                                          Br 5-chloromethylisoxazolyl-3                                    __________________________________________________________________________

The active ingredients have a strong action on microorganisms. They prevent and heal plant diseases caused by fungi, e.g., Botrytis cinerea in grapes and strawberries, Monilia fructigens in apples, Cercospora arachidicola in groundnuts, Phytophthora infestans in potatoes and tomatoes, Plasmopara viticola in grapes, Alternaria solani in tomatoes, and Helminthosphorium teres and Septoria nodorum in cereals.

The compounds are also effective on phytopathogenic bacteria such as Erwinia amylovora in pears and apples, Erwinia carotova in potatoes, Pseudomonas lachrymans in cucumbers, Pseudomonas phaseolicola in beans, and Xanthomonas oryzae in rice.

Application may be effected for instance in the form of directly sprayable solutions, powders, suspensions (including high-percentage aqueous, oily or other suspensions), dispersions, emulsions, oil dispersions, pastes, dusts, broadcasting agents, or granules by spraying, admixing while stirring, trowelling, painting, impregnating, atomizing, dusting, broadcasting or watering. The forms of application depend entirely on the purpose for which the agents are being used, but they must ensure as fine a distribution of the novel active ingredients as possible.

For the preparation of solutions, emulsions and oil dispersions to be sprayed direct, mineral oil fractions of medium to high boiling point, such has kerosene or diesel oil, further coal-tar oils, and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons such as toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives such as methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, etc., and strongly polar solvents such as dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, and particularly water are suitable.

Aqueous formulations may be prepared from emulsion concentrates, pastes, oil dispersions or wettable powders by adding water. To prepare emulsions, pastes and oil dispersions the ingredients as such or dissolved in an oil or solvent may be homogenized in water by means of wetting or dispersing agents, adherents or emulsifiers. Concentrates which are suitable for dilution with water may be prepared from active ingredient, wetting agent, adherent, emulsifying or dispersing agent and possibly solvent or oil.

Examples of surfactants are: alkali metal, alkaline earth metal and ammonium salts of ligninsulfonic acid, naphthalenesulfonic acids, phenolsulfonic acids, alkylaryl sulfonates, alkyl sulfates, and alkyl sulfonates, alkali metal and alkaline earth metal salts of dibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, alkali metal and alkaline earth metal salts of fatty acids, salts of sulfated hexadecanols, heptadecanols, and octadecanols, salts of sulfated fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, ethoxylated octylphenol and ethoxylated nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin, sulfite waste liquors and methyl cellulose.

Powders, dusts and broadcasting agents may be prepared by mixing or grinding the active ingredients with a solid carrier.

Granules, e.g., coated, impregnated or homogeneous granules, may be prepared by bonding the active ingredients to solid carriers. Examples of solid carriers are mineral earths such as silicic acid, silica gels, silicates, talc, kaolin, attapulgus clay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, and ureas, and vegetable products such as grain flours, bark meal, wood meal, and nutshell meal, cellulosic powders, etc.

Examples of formulations are given below.

I. 90 parts by weight of compound 1 (the compound of Example 1) is mixed with 10 parts by weight of N-methyl-alpha-pyrrolidone. A mixture is obtained which is suitable for application in the form of very fine drops.

II. 20 parts by weight of compound 2 is dissolved in a mixture consisting of 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into water and uniformly distributing it therein, an aqueous dispersion is obtained.

III. 20 parts by weight of compound 24 is dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide and 1 mole of isooctylphenol, and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into water and finely distributing it therein, an aqueous dispersion is obtained.

IV. 20 parts by weight of compound 43 is dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210 g and 280° C., and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into water and uniformly distributing it therein, an aqueous dispersion is obtained.

V. 80 parts by weight of compound 111 is well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-alpha-sulfonic acid, 10 parts by weight of the sodium salt of a lignin-sulfonic acid obtained from a sulfite waste liquor, and 7 parts by weight of powdered silica gel, and triturated in a hammer mill. By uniformly distribution the mixture in water, a spray liquor is obtained.

VI. 5 parts by weight of compound 196 is intimately mixed with 95 parts by weight of particulate kaolin. A dust is obtained containing 5% by weight of the active ingredient.

VII. 30 parts by weight of compound 214 is intimately mixed with a mixture consisting of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. A formulation of the active ingredient is obtained having good adherence.

VIII. 40 parts by weight of compound 503 is intimately mixed with 30 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts of water to give a stable aqueous dispersion.

IX. 20 parts of compound 904 is intimately mixed with 2 parts of the calcium salt of dodecylbenzenesulfonic acid, 8 parts of a fatty alcohol polyglycol ether, 2 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts of a paraffinic mineral oil. A stable oily dispersion is obtained.

The active ingredients may also be applied together with other active ingredients, e.g., herbicides, insecticides, growth regulators, and other fungicides, or in admixture with fertilizers. Mixing with other fungicides frequently results in a greater fungicidal action spectrum; with some of these fungicidal mixtures synergistic effects also occur, i.e., the fungicidal action of the combination is greater than the sum of the effects of the individual components.

The novel compounds may be employed not only in crop protection, but also for protecting various materials against degradation or destruction by bacteria or fungi. Examples of materials which can be preserved or microbicidally finished withn the novel compounds are adhesives and glues, plastics dispersions, emulsion paints, coatings in high-humidity rooms, textiles, leather, raw hides, wood and plastics, especially soft PVC.

Generally, the formulations contain from 0.1 to 95, and preferably 0.5 to 90. wt% of active ingredient. The application rates depend on the type of effect desired, and range from 0.001 to 5, preferably 0.01 to 5, wt%, based on the weight of the material to be protected; in agriculture, the rates vary from 0.1 to 5 kg/ha.

The following microorganisms, for instance, may be controlled with the compounds according to the invention in the protection of materials: Chaetomium globosum, Chaetomium alba, Aspergillus terreus, Aspergillus niger, Aspergillus versicolor, Penicillium glaucum, Pennicilium funiculosum, Trichoderma viride, Aureobasidium pullulans, Cladosporium herbarum, Cladosporium resinae, Humicola grisea, Glenospora graphii, Phoma violacea; Streptomyces albus; Staphylococcus aureus, Escheria coli, Pseudomonas aeruginosa, Aerobactera aerogenes, and Serratia marcescens.

The following list of fungicides with which the novel compounds may be combined in intended to illustrate possible combinations but not to impose any restrictions.

Examples of fungicides which may be combined with the novel compounds are:

sulfur,

dithiocarbamates and heir derivatives, such as

ferric dimethyldithiocarbamate,

zinc dimethyldithiocarbamate,

zinc ethylenebisdithiocarbamate,

manganese ethylenebisdithiocarbamate,

manganese zinc ethylenediaminebisdithiocarbamate,

tetramethylthiuram disulfides,

ammonia complex of zinc, N,N'-ethylenebisdithiocarbamate

ammonia complex of zinc N,N'-propylenebisdithiocarbamate,

zinc N,N'-propylenebisdithioccarbamate and

N,N'-polypropylenebis(thiocarbamyl) disulfide;

nitro derivatives, such as

dinitro(1-methylheptyl)-phenyl crotonate,

2-sec-butyl-4,6-dinitrophenyl 3,3-dimethylacrylate,

2-sec-butyl-4,6-dinitrophenyl isopropylcarbonate and

diisopropyl 5-nitroisophthalate;

heterocyclic substances, such as

2-heptadecyldimidazol-2-yl acetate,

2,4-dichloro-6-(o-chloroanilino)-s-triazine,

O,O-diethyl phthalimidophosphonothioate,

5-amino-1-[-bis-(dimethylamino)-phosphinyl]-3-phenyl-1,2,4-triazole,

2,3-dicyano-1,4-dithiaanthraquinone,

2-thio-1,3-dithio[4,5-b]quinoxaline,

methyl 1-(butylcarbamyl)-2-benzimidazolecarbamate,

2-methoxycarbonylaminobenzimidazole,

2-(fur-2-yl)-benzimidazole,

2-(thiazol-4-yl)benzimidazole,

N-(1,1,2,2-tetrachloroethylthio)-tetrahydrophthalimide,

N-trichloromethylthiotetrahydrophthalimide,

N-trichloromethylthiophthalimide,

N-dichlorofluoromethylthio-N',N'-dimethyl-N-phenylsulfuric acid diamide,

5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole,

2-thiocyanatomethylthiobenzothiazole,

1,4-dichloro-2,5-dimethoxybenzene,

4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone,

8-hydroxyquinoline and its copper salt,

2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin,

2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin 4,4-dioxide,

2-methyl-5,6-dihydro-5H-pyran-3-carboxanilide,

2-methylfuran-3-carboxanilide,

2,5-dimethylfuran-3-carboxanilide,

2,4,5-trimethylfuran-3-carboxanilide,

2,5-dimethyl-N-cyclohexylfuran-3-carboxamide,

N-cyclohexyl-N-methoxy-2,5-diethylfuran-3-carboxamide,

2-methylbenzanilide,

2-iodobenzanilide,

N-formyl-N-morpholine-2,2,2-trichloroethylacetal,

piperazine-1,4-diylbis-(1-(2,2,2-trichloroethyl)-formamide),

1-(3,4-dichloroanilino)-1-formylamino-2,2,2-trichloroethane,

2,6-dimethyl-N-cyclododecylmorpholine and its salts,

N-[3-(p-tert.butylphenyl)-2-methylpropyl]-cis-2,6-dimethylmorpholine,

N-[3-(p-tert.-butylphenyl)-2-methylpropyl]-piperidine,

1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole

1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole,

N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N'-imidazolyl-urea,

1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-butan-2-one,

1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-butan-2-ol,

1-(4-phenylphenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol,

α-(2-chlorophenyl)-α-(4-chlorophenyl)-5-pyrimidinemethanol,

5-butyl-(2-dimethylamino-4-hydroxy-6-methylpyrimidine,

bis-(p-chlorophenyl)-3-pyridinemethanol,

dodecylguanidine acetate,

3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]-glutaramide,

hexachlorobenzene,

DL-methyl-N-(2,6-dimethylphenyl)-N-fur-2-yl alanate,

methyl DL-N-(2,6-dimethylphenyl)-N-(2'-methoxyacetyl)-alanate,

N-(2,6-dimethylphenyl)-N-chloroacetyl-DL-2-aminobutyrolactone,

methyl DL-N-(2,6-dimethylphenyl)-N-(phenylacetyl)-alanate,

5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine,

3-[3,5-dichlorophenyl]-5-methyl-5-methoxymethyl-1,3-oxazolidine-2,4-dione,

3-(3,5-dichlorophenyl)-1-isopropylcarbamylhydantoin,

N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide,

2-cyano-[N-(ethylaminocarbonyl)-2-methoximino]-acetamide,

1-[2-(2,4-dichlorophenyl)-pentyl]-1H-1,2,4-triazole,

2,4-difluoro-α-(1H-1,2,4-triazol-1-ylmethyl)-benzhydryl alcohol,

1-[bis-(4-fluorophenyl)-methylsilyl]-methyl-1H-1,2,4-triazole,

pyridine-2-mercapto-oxide,

2-[N-(3-chloro-2,6-dinitro-4-trifluoromethylphenylamino]-5-trifluoromethyl-3-chloropyridine,

1,2-bis-(3-methoxycarbonyl-2-thioureido)-benzene,

1,2-bis-(3-ethoxycarbonyl-2-thioureido)-benzene.

In the use example below, the following compounds were employed for comparison purposes:

A: 5-chloro-8-(4'-methyl-1',2',3'-thiadiazol-5'-carbonyloxy)-quinoline (EP98, 486, Example 128);

B: 8-α-furoyloxy-5-methylquinoline (British Pat. No. 1,141,697, Example 1);

C: 5-acetyl-7-nitro-8-(1',2',3'-thiadiazol-4-carbonyloxy)-quinoline (DE No. 3,225,169, Example 24);

D: 7-nitro-8-(α-thenoyloxy)-quinoline (DE No. 2,005,959, Example 38).

Use examples Example I

Action on Botrytis cinerea in pimientos

Pimiento seedlings of the "Neusiedler Ideal Elite" variety were sprayed, after 4 to 5 leaves were well developed, to runoff with aqueous suspensions containing (dry basis) 80% of active ingredient and 20% of emulsifier. After the sprayed-on layer had dried, the plants were sprinkled with a conidial suspension of the fungus Botrytis cinerea, and placed at 22° to 24° C. in a high-humidity chamber. After 5 days, the disease had spread to such a great extent on the untreated plants that the necroses covered the major portion of the leaves.

The compounds of Examples 1, 111, 298, 300, 301, 332, 342, 368, 384, 386, 427, 627 and 815 proved to be extremely effective and far superior to comparative agents A and D.

Example II

Action on Phytophthora infestans in tomatoes

Leaves of potted tomatoes of the "GroBe Fleischtomate" variety were sprayed with aqueous liquors containing (dry basis) 80% of active ingredient and 20% of emulsifier. After 24 hours the leaves were infected with a zoospore suspension of the fungus Phytophtora infestans. The plants were then placed for 6 days in a water vapor-saturated chamber at 16° to 18° C. After this period, the disease had spread on the untreated control plants to such an extent that the fungicidal action was able to be assessed.

The compounds of Examples 1, 2, 85, 256, 300, 301, 368, 384, 427, 469, 471 and 818 had an excellent action which was far superior to that of comparative agents A and B.

Example III

Action on Pyrenophora teres

Leaves of barley seedlings of the "Asse" variety, in the two-leaf stage, were sprayed on runoff with aqueous suspensions containing (dry basis) 80% of active ingredient and 20% of emulsifier. After 24 hours the plants were inoculated with a spore suspension of the fungus Pyrenophora teres and placed for 48 hours in a high-humidity climatic cabinet at 18° C. The plants were then cultivated for a further 5 days in the greenhouse at 20° to 22° C. and a relative humidity of 70%. The spread of the symptoms was then determined.

The compounds of Examples 85, 300, 386, 427, 973 and 1256 proved to be not only highly effective, but also far superior to comparative agent B.

Example IV

Fungicidal action on Aspergillus niger

The active ingredients were added, in amounts of 100, 50, 25, 10, 5 and 1 parts by weight per million parts of solution, to a nutrient solution ideally suited for promoting the growth of the fungus Aspergillus niger. 20 ml of the nutrient solution treated in this manner was introduced into 100 ml glass flasks and inoculated with 0.3 mg of Aspergillus spores. After the flasks had been incubated for 120 hours at 36° C., the extent of fungus spread (predominantly on the surface of the nutrient solution) was assessed.

The compounds of Examples 1, 2, 24, 43, 127, 196, 212, 214, 215, 298, 300, 342, 384, 427, 469, 471, 729, 731 and 732 had an excellent action which was far superior to that of comparative agent C.

Example V

Fungicidal action on Aureobasidium pullulans

To determine the action on Aureobasidium pullulans, the active ingredients were added, in amounts of 100, 50, 25, 12, 6, 3 and 1.5 parts by weight per million parts of solution, to a nutrient solution ideally suited for promoting the growth of the fungus. 10 ml of this mixture of nitrient solution and active ingredient was introduced into sterile test tubes and inoculated with one drop of a spore suspension containing 10⁶ conidia or cells. After 120 hours' incubation, samples were removed from those tubes showing no visible signs of fungus growth and transferred to fungus nutrient media. In this way those amounts of active ingredient were determined at which no more fungus growth occurred after transfer of a sample to the nutrient medium.

The compounds of Examples 24, 43, 74, 127, 196 and 732 were good to very good, and those of Examples 212, 214, 215, 298, 300, 342, 427, 729 and 731 excellent.

Example VI

Bactericidal action on Staphylococcus aureus and Escheria coli

The bacteria kill values were determined as follows:

5 ml of a doubly concentrated nutrient broth was added to 5 ml of a dilution of the agents in water in sterile test tubes, and mixed. The tubes were then inoculated by adding one drop of a 16-hour old broth culture (diluted 1:10) of the bacteria species Staphylococcus aureus and Escheria coli, and incubated for 24 hours at 37° C. After this time, samples were transferred from the tubes to bacteria nutrient media, which were then also incubated for 24 hours at 37° C. The dilution stage at which no bacterial growth occurred after transfer of a sample to the nutrient medium was taken as the kill value.

The compounds of Examples 2, 298,300 and 427 were highly effective. 

We claim:
 1. A quinoline derivative of the formula ##STR7## where R¹ is hydrogen or methyl, R² is hydrogen or halogen, R³ is hydrogen, methyl, halogen or nitro, R⁴ is hydrogen, halogen or nitro, and R⁵ is a thiophene, pyrrole, oxazole, thiazole, imidazole, isoxazole, isothiazole, pyrazole, 1,2,3-, 1,2,4-, 1,2,5- or 1,3,4-oxadiazole or 1,2,3- or 1,2,4-triazole radical which is unsubstituted or monosubstituted or disubstituted by C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, nitro or halogen, the substituents being independent of one another in the case of disubstitution, or is furan which is substituted by halogen or monosubstituted or disubstituted by methyl, and R³ and R⁴ are not simultaneously halogen, with the reception of 5-chloro-, 2-methyl- and 5-nitro-8-(1',2',3'-thiadiazole-4'-carbonyloxy)-quinoline, 5-chloro-8-(4'-methyl-1',2',3'-thiadiazole-4'-carbonyloxy)-quinoline, 5-methyl-, 5-methyl-7-nitro-, 5-methyl-7-halo- and 7-nitro-8-(α-thenoyloxy)-quinoline, 5-nitro- and 5-methyl-7-nitro-8-(2'-halofuroyl-5'-oxy)-quinoline and 2-methyl-8-(isoxazole-5'-carbonyloxy)-quinoline.
 2. A quinoline derivative of the formula I as set forth in claim 1, where R¹ is hydrogen, R², R³ and R⁴ have the meanings given in claim 1, and R⁵ is an unsubstituted or chloromethyl-substituted isoxazol-3-yl or isoxazol-5-yl radical, an unsubstituted or methyl-substituted oxazol-5-yl radical, an imidazol-1-yl radical or an unsubstituted or methyl-substituted 1,2,3-thiadiazol-4-yl or 1,2,3-thiadiazol-5-yl radical.
 3. A quinoline derivative of the formula I as set forth in claim 1, where R¹ and R² are hydrogen, R³ and R⁴ are independent of each other and are hydrogen, halogen or nitro, and R⁵ has the meanings given in claim 1, with the proviso that R³ and R⁴ are simultaneously neither hydrogen nor halogen.
 4. A quinoline derivative of the formula I as set forth in claim 1, where R¹ and R² are hydrogen, R³ and R⁴ are independently of each other and are hydrogen, halogen or nitro, and R⁵ has the meanings given in claim
 2. 5. A microbicidal composition containing a carrier and an effective amount of a quinoline derivative of the formula ##STR8## where R¹ is hydrogen or methyl, R² is hydrogen or halogen, R³ is hydrogen, methyl, halogen or nitro, R⁴ is hydrogen, halogen or nitro, and R⁵ is a thiophene, pyrrole, oxazole, thiazole, imidazole, isoxazole, isothiazole, pyrazole, 1,2,3-, 1,2,4-1,2,5- or 1,3,4-oxadiazole or 1,2,3-or 1,2,4-triazole radical which is unsubstituted or monosubstituted or disubstituted by C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, nitro or halogen, the substituents being independent of one another in the case of disubstitution, or is furan which is substituted by halogen or monosubstituted or disubstituted by methyl, and R³ and R⁴ are not simultaneously halogen, with the exception of 5-chloro-, 2-methyl- and 5-nitro-8-(1',2',3'-thiadiazole-4'-carbonyloxy)-quinoline, 5-chloro-8-(4'-methyl-1',2',3'-thiadiazole-5'-carbonyloxy)-quinoline, 5-methyl-, 5-methyl-7-nitro-, 5-metyl-7-halo-and 7-nitro-8-(α-thenoyloxy)-quinoline, 5-nitro- and 5-metyl-7-nitro-8-(2' -halofuroyl-5'-oxy)-quinoline and 2-methyl-8-(isoxazole-5'-carbonyloxy)-quinoline.
 6. A process for combating bacteria or fungi, wherein an effective amount of a quinoline derivative of the formula ##STR9## where R¹ is hydrogen or methyl, R² is hydrogen or halogen, R³ is hydrogen, methyl, halogen or nitro, R⁴ is hydrogen, halogen or nitro, and R⁵ is a thiophene, pyrrole, oxazole, thiazole, imidazole, isoxazole, isothiazole, pyrazole, 1,2,3-, 1,2,4-, 1,2,5- or 1,3,4-oxadiazole or 1,2,3- or 1,2,4-triazole radical which is unsubstituted or monosubstituted or disubstituted by C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, nitro or halogen, the substituents being independent of one another in the case of disubstitution, or is furan which is substituted by halogen or monosubstituted or disubstituted by metyl, and R³ and R⁴ are not simultaneously halogen, with the exception of 5-chloro-, 2-methyl- and 5-nitro-8-(1',2',3'-thiadiazole-4'-carbonyloxy)-quinoline, 5-chloro-8-(4'-methyl-1',2',3'-thiadiazole-5'-carbonyloxy)-quinoline, 5-metyl-, 5-methyl-7-nitro-, 5-methyl-7-halo-and 7-nitro-8-(α-thenoyloxy)-quinoline, 5-nitro- and 5-methyl-7-nitro-8-(2'-halofuroyl-5═-oxy)-quinoline and 2-methyl-8-(isoxazole-5'-carbonyloxy)-quinoline, is allowed to act on bacteria or fungi, or on materials, soil, plants or seed threatened by bacterial or fungal attack.
 7. A quinoline derivative of the formula I as set forth in claim 1, wherein R¹, R² and R⁴ are each hydrogen, R³ is NO₂ and R⁵ is isoxazolyl-5. 